Month: May 2021

Reference of 454-78-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: tert-Butyl 4-[2-chloro-5-(trifluoromethyl)phenyl]piperazine-1-carboxylate Into a 50 mL pressure vial equipped with a magnetic stir bar was added tert-butyl piperazine-1-carboxylate (2.00 g, 10.7 mmol), palladium(II) acetate (0.24 g, 1.07 mmol) and racemic-BINAP (1.34 g, 2.15 mmol). The vial was evacuated under vacuum (1 mm Hg) and backfilled with N2 (repeated 3 times). Toluene (10 mL) and 3-bromo-4-chlorobenzotrifluoride (3.06 g, 11.8 mmol) were added to the vial and the solvent was degassed for 10 min with a steady flow of nitrogen before being heated to 120 C. for 16 h. The reaction mixture was filtered through a plug of celite on a sintered glass funnel, washing with diethyl ether (100 mL). The filtrate was concentrated and purified by column chromatography through silica gel, eluting with 0% EtOAc in hexanes to 40% EtOAc in hexanes as a gradient. The desired product was obtained as a light yellow oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Isabel, Elise; Lachance, Nicolas; Leclerc, Jean-Philippe; Leger, Serge; Oballa, Renata M.; Powell, David; Ramtohul, Yeeman K.; Roy, Patrick; Tranmer, Geoffrey K.; Aspiotis, Renee; Li, Lianhai; Martins, Evelyn; US2011/301143; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 3260-88-6, These common heterocyclic compound, 3260-88-6, name is 2-Methyl-3-chloroanisole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a 250 mL round bottom flask, l-chloro-3-methoxy-2-methylbenzene (5.0 g, 31.9 mmol) was dissolved in CCLt (5OmL). To the solution, l-bromopyrrolidine-2,5-dione (5.8 g, 32.6 mmol) and benzoyl benzenecarboperoxoate (70 mg) were added in sequence. The resulting mixture was refluxed for 4 hours and left at room temperature overnight. The mixture was filtered. The filtrate was evaporated to provide crude product of 2-(bromomethyl)-l-chloro-3-methoxybenzene as a colorless liquid, which was used for next step without further purification.

Statistics shows that 2-Methyl-3-chloroanisole is playing an increasingly important role. we look forward to future research findings about 3260-88-6.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 120758-03-4, name is 2-Chloro-3,5-dimethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Chloro-3,5-dimethoxyaniline

Step 4 14.4 g of potassium isocyanate were dissolved at 10 C. in 450 ml of acetone. 14.2 ml of benzoylchloride were added dropwise carefully. The white suspension was refluxed 10 minutes and then cooled again to 10 C. A solution of 28 g of 2-chloro-3,5-dimethoxyaniline in 300 ml of acetone was then added and the obtained mixture refluxed over 3 h. 700 ml of water with ice were added and the aqueous phase was extracted with 3*600 ml of ethyl acetate. The organic phase was then dried over magnesium sulfate and concentrated. The brown residue was dissolved in 100 ml ethanol and refluxed together with 35 ml of an aqueous solution of potassium hydroxide. After 1 hour, 500 ml of water were added. Ethanol was distilled under reduced pressure. The brown solution was neutralized with 300 ml of an ammonium chloride solution and the solid which precipitated was filtered, washed with water and dried. 35 g of (2-chloro-3,5-dimethoxy-phenyl)-thiourea were obtained as a brown powder, m.p. 159-162 C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 120758-03-4.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US2003/162822; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5ClF3N

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

According to the analysis of related databases, 69411-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 454-78-4, A common heterocyclic compound, 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of l-bromo-2-chloro -4-(trifluoromethyl)benzene (1.5 mL, 10 mmol) in 30 mL of anhydrous THF was added Pd(PPh3)2Cl2 (351mg, 0.5 mmol), triphenylphosphine (65 mg, 0.25 mmol), ethynyl(trimethyl)silane (2.12 mL, 15 mmol), and triethylamine (2.1 mL, 15 mmol). The reaction was stirred at room temperature for 20 minutes after which CuI (23 mg, 0.12 mmol) was added to the solution and the reaction was stirred at room temperature for 16 hours. The reaction was then concentrated in vacuo and the resulting residue was dissolved in hexanes, filtered through Celite and again concentrated in vacuo. The residue was purified by flash column chromatography using 100% hexanes to afford the desired product as a dark brown oil. 1H NMR (CDCl3, 500MHz: 7.8 (d, 7=1.6 Hz, IH), 7.5 (m, 2H), 0.23 (s, 9H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK & CO., INC.; WO2006/14618; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 454-78-4,Some common heterocyclic compound, 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1: To a 500 mL three-neck RBF equipped with a magnetic stirring bar were added, under N2 atmosphere, 3-bromo-4-chloro-benzotrifluoride (16.5 mL, 110 mmol) and dry THF (150 mL). The resulting solution was cooled to 0 C. To this solution was added z’-PrMgBr (110 mL, 110 mmol) and the reaction was warmed to rt and stirred for 1 h. To another 500 mL RBF containing a solution of CuBr Me2S (18.8 g, 91.5 mmol) in THF (100 mL) was added BF3*OEt2 (14 mL, 110 mmol) dropwise at -40 C. The resulting solution was stirred at that temperature for 45 min. Then, the Grignard reagent prepared previously was added dropwise to this solution while maintaining the internal temperature at -32 to -38 C. After completion of addition, the reaction mixture was stirred at that temperature for 1 h. The reaction mixture was cooled to -78 C, and a solution of (2S)-l-t-butyl 2-ethyl 5-methoxypyrrolidine-l ,2- dicarboxylate (25.0 g, 91.5 mmol) in THF (50 mL) was added dropwise. The resulting reaction mixture was allowed to warm up to rt and was stirred for 14 h. The reaction mixture was cooled to 0 C, and saturated aqueous NH4C1 solution (100 mL) was added followed by aqueous NH4OH solution (100 mL) and water (300 mL). The layers were separated. The aqueous layer was extracted with EtOAc (3 x 200 mL). The combined organics were dried over anhydrous Na2S04 and concentrated. The crude product was purified by column chromatography eluting with 5% EtOAc in petroleum ether to yield (2S,5S)-l-tert-butyl 2-ethyl 5-(2-chloro-5- (trifluoromethyl)phenyl)pyrrolidine-l,2-dicarboxylate (34.0 g, 79.8 mmol) as a colorless liquid. 1H NMR (400 MHz, CDC13) 7.32-7.47 (m, 3 H), 5.39-5.50 (m, 1 H), 4.58-4.70 (m, 1 H), 4.22- 4.28 (m, 2 H), 2.55 (m, 1 H), 2.18 (m, 1 H), 2.05 (m, 1 H), 1.83 (m, 1 H), 1.16-1.43 (m, 12 H); LC-MS ESI calc’d. for Ci9H23ClF3N04 [M-Boc]+ 321.84, found 322.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; SHAO, Pengcheng Patrick; KRIKORIAN, Arto, D.; VACHAL, Petr; WO2015/17302; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 167404-32-2, name is 4-Cyclopropylbenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Cyclopropylbenzene-1-sulfonyl chloride

In a flame dried flask under N2 blanket, compound D (1.5 g, 4.9 MMOL) was dissolved in dry THF (30 mL) and COOLED TO-78C. N-BUTYL lithium (1.9 M in hexanes, 5.4 mL, 9.7 MMOL) was added followed after 45 min by compound E (1.27 g, 6.3 MMOL). The cold bath was removed after 2 h and the reaction mixture was allowed to warm to rt over 45 minutes then quenched with aq NH4CI. EtOAc (30 mL) was added to dilute the reaction mixture. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (25% EtOAc/Hexanes) to give 545 mg (27%) of compound F. Compound i (120 g, 1.0 mml) was dissolved in CH2CI2 (1.2 L) with HG20 (6.0 g, 14.4 MMOL) and K2CO3 (24.0 g, 0.17 mol) and cooled to-30 C. Br2 (85.2 g, 1.1 mol) was added over 10 min period of time. The reaction mixture was stirred at-30 C for 4.5 h. The reaction mixture was washed with H20 (1 L) and brine (1 L). The organic layer was dried over NA2SO4 and concentrated to dryness. The crude material was distilled under reduced pressure to give 103.8 g (52%) of compound ii. In a flame dried flask under N2 blanket, compound ii (6.0 g, 30.5 MMOL) was dissolved in dry THF (30 mL) and cooled TO-78 C. A solution of n-butyl lithium (1.75 M in hexanes, 17.4 mL, 30.5 MMOL) was added and the reaction mixture was stirred for 20 min. S02 was bubbled in the reaction for 20 min. It was slowly warmed up to rt. CH2CI2 (50 mL) was added and the mixture was reacted with NCS (5.0 g, 37.4 MMOL) at rt overnight. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (5% EtOAC/Hexanes) to give 3.65 g (55%) of compound II. To a round-bottom flask was added compound iii (3.0 g, 13.8 MMOL) and KF (2.4 g, 41.4 MMOL) followed by addition of acetone (50 mL) and water (30 mL). The reaction mixture was stirred at room temperature overnight. The solvent was then removed. Methylene chloride (40 mL) was added and it was washed with brine (40 mL). The organic layer was dried over NA2SO4 and then concentrated to dryness to give 2.77 g (100%) of compound E.

The synthetic route of 167404-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2004/48322; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 64473-35-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 64473-35-4 name is 1-(3-Bromopropyl)-4-chlorobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1 3-(4-Chlorophenyl)propylamine The potassium salt of phthalimide (4.4 g, 24 mmol) was dissolved in DMF (20 ml) and 1-chloro-4-(3-bromopropyl)benzene (4.67 g, 20 mmol) was added. The mixture was stirred at 80 C. for 16 hours. Water (50 ml) and DCM (50 ml) were added, the phases were separated and the aqueous phase extracted with DCM (2*50 ml). The combined organic phases were washed with sodium hydroxide (0.2 M, 50 ml), dried (magnesium sulphate), filtered and concentrated in vacuo. Ethanol (75 ml) and hydrazine hydrate (2 equiv.) were added and the mixture was heated to reflux for 2 hours. After cooling the mixture was filtrated and the filter cake washed with DCM (2*50 ml). The filtrate and washings were evaporated and dissolved in ethyl acetate (40 ml). Washing of the organic phase with sodium hydroxide (0.4 M, 2*25 ml) and water (2*25 ml) followed by drying (magnesium sulphate), filtration and evaporation gave 3-(4-chlorophenyl)propylamine. 1H NMR (CDCl3): delta1.82-1.50 (m, 4H); 2.78-2.53 (m, 4H); 7.32-6.96 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Bromopropyl)-4-chlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Andersen, Knud Erik; Dorwald, Florencio Zaragiza; Peschke, Bernd; Sidelmann, Ulla Grove; Rudolf, Klaus; Stenkamp, Dirk; Hurnaus, Rudolf; Muller, Stephan Georg; Krist, Bernd; Eriksen, Birgitte; US2002/58659; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H4ClN3

Reference Example 11 3-{[2-(Trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one [Show Image] Diethoxymethyl acetate (15 mL) was added to 2-chloropyridine-3,4-diamine (480 mg) and the resulting mixture was stirred at room temperature for 12 hours. To the mixture was added 1N hydrochloric acid and the precipitate formed was filtered, washed with diethyl ether and then dried to obtain a crude product (400 mg), 4-chloro-1H-imidazo[4,5-c]pyridine as a brown solid. The spectrum of this compound is as follows: 1H NMR (400 MHz, CD3OD) delta 9.45 (s, 1H), 8.51 (d, J = 5.9 Hz, 1H), 7.94 (d, J = 5.9 Hz, 1H). MS (ESI+) 154 (M+ +1, 100%). A hydrochloric acid/methanol solution (25 mL, methanol component 80-90%) was added to this solid (220 mg) and the resulting mixture was heated under reflux for 30 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure, and the resulting residue was washed with diethyl ether and dried to obtain a crude product (150 mg), 3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one as a brown solid. The spectrum of this compound is as follows: 1H NMR (400 MHz, CD3OD) delta 9.40 (s, 1H), 7.58 (d, J = 7.2 Hz, 1H), 6.87 (d, J = 7.2 Hz, 1H). MS (ESI+) 136 (M++1, 100%). Under a nitrogen atmosphere, sodium hydride (134 mg, a 60% oil dispersion) was added to N,N-dimethylformamide (15 mL) and the resulting suspension was cooled to -15C. To the suspension was added 3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (360 mg) and the resulting mixture was stirred at room temperature for 30 minutes. Then, chloro-2-(trimethylsilyl)ethoxymethane (0.550 mL) was added dropwise thereto, followed by stirring at room temperature for 20 hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (developing solvent: chloroform/methanol = 20/1 to 10/1) to obtain 3-{[2-(trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (119 mg) and 1-{[2-(trimethyl-silyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (113 mg) each as a white solid. 3-{[2-(Trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1H NMR (400 MHz, CDCl3) delta 11.49 (bs, 1H), 8.03 (s, 1H), 7.16 (m, 1H), 6.77 (d, J = 7.0 Hz, 1H), 5.91 (s, 2H), 3.66 (t, J = 8.2 Hz, 2H), 0.93 (t, J = 8.2 Hz, 2H), – 0.04 (s, 9H). MS (ESI+) 266 (M++1, 100%). 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1H NMR (400 MHz, CDCl3) delta 10.97 (bs, 1H), 7.84 (s, 1H), 7.21 (m, 1H), 6.56 (d, J = 7.1 Hz, 1H), 5.45 (s, 2H), 3.51 (t, J = 8.2Hz, 2H), 0.90 (t, J = 8.2 Hz, 2H), – 0.03 (s, 9H). MS (ESI+) 266 (M++1, 100%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2770-01-6.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1690863; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

54730-35-7, name is 3,5-Dichloro-4-methylaniline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: chlorides-buliding-blocks

Transferred 3,5-dichloro-4-methylaniline (0.28 g, 1.59 mmol, Eq: 1.00) to a 50-mL round-bottomed flask using dichoromethane (10 mL). Added Iota,Gamma-thiocarbonyldiimidazole (429 mg, 2.41 mmol, Eq: 1.51) and stirred overnight at room temperature. HPLC showed no starting material remaining. Concentrated the reaction mixture onto silica. Purified using a 12 g silica column on an Intelliflash 280; collected peaks only in 9 mL fraction at 32 mL/min; equilibrated with heptane; dry loaded; eluted 1 min with heptane; increased from 0 – 10%> dichloromethane/heptane over 5 min. Obtained 226 mg (65%) of l,3-dichloro-5-isothiocyanato- 2-methylbenzene as a yellow solid.

The synthetic route of 54730-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics