Tag: M.W=200-300

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. 33863-76-2 name is 1-Bromo-3-chloro-5-fluorobenzene, 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. 33863-76-2

To a solution of 1-bromo-3-chloro-5-fluorobenzene (25 g, 120 mmol) in methanol (800 ml) was added sodium methoxide (64 g, 1180 mmol). The reaction was heated to reflux for 9 days. The reaction was then concentrated in vacuo to one fifth of the volume (150 ml), cooled, and water (1000 ml) added. The mixture was extracted with diethyl ether (3 x 150 ml). The combined organic extracts were washed with brine (2 x 100 ml), dried over Na2SO4 and evaporated to afford the title compound (24.6 g). 1HNMR (CDCI3): 3.80(s, 3H), 6.84(s, 1 H), 6.96(s, 1 H), 7.10 (s, 1 H)GCMS Rt=3.86min MS m/z 222 [MH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

60811-21-4, A common compound: 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a microwave vial equipped with a stir bar, 4-bromo-2-chloro-1-fluorobenzene (1 equiv, Combi-Blocks, CAS 60811-21-4), oxetan-3-ol (10 equiv) and Cs2CO3 (1 equiv) were combined. The vial was sealed, degassed and heated to 120 C. for 20 hours in an oil bath. The reaction mixture was purified by reverse-phase column chromatography using a C18 cartridge on an automated Teledyne ISCO Rf machine, eluting with 10% to 100% acetonitrile in water+0.1% formic acid as a gradient over 20 minutes. The fractions containing the desired compound were combined and concentrated under vacuum to provide the title compound

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, 4-Bromo-2-chloro-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tempest Therapeutics, Inc.; BRAVO, Yalda; CHEN, Austin Chih-Yu; DING, Jinyue; GOMEZ, Robert; LAM, Heather; NAGAMIZO, Joe Fred; OBALLA, Renata Marcella; POWELL, David Andrew; SHENG, Tao; (190 pag.)US2019/315712; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6579-54-0, The chemical industry reduces the impact on the environment during synthesis 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, I believe this compound will play a more active role in future production and life.

171 mg 3-[6-(2-Methoxy-phenyl)-pyrimidin-4-ylamino]-benzyl-ammonium chloride (prepared in Example 69) (0.5 mmol) was dissolved in 50 cm3 dry dichloromethane, 0.350 cm3 N,N-diisopropyl-ethylamine (259 mg, 2 mmol) was added and the mixture was cooled to 0 C. in an ice bath. After stirring it for 15 minutes 196 mg 2,6-dichlorobenzenesulfonyl-chloride (0.8 mmol) was added and the mixture was stirred for 2 hours at 0 C. and overnight at room temperature. Then 50 cm3 5% NaHCO3 solution was added and it was extracted three times with 50-50 cm3 of chloroform. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated under reduced pressure. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product as an yellow solid. Yield: 34 mg (13%). For analitical results and compound identification see Table 1.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichlorobenzenesulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Greff, Zoltan; Varga, Zoltan; Keri, Gyoergy; Nemeth, Gabor; Oerfi, Laszlo; Szantai Kis, Csaba; US2012/258968; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2770-11-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2770-11-8 as follows.

Preparation of {4-[2-(4-chlorophenoxy)phenylamino]-piperidin-l-yl}- cyclohexylmethanone STX1702 C24H29ClN2O2, MW: 396.9785 EPO To a solution of 2-(4-chlorophenoxy)phenylamine (100 mg, 0.49 mmol), 1- cyclohexanecarbonyl-4-piperidone (154 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 1000C for 15 minutes in a CEM discover microwave (fixed hold time set to on). Further l-cyclohexanecarbonyl-4-piperidone (50 mg, 0.24 mmol) was added and this reaction mixture was again heated at 1000C for 10 minutes in the CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) followed. The combined organics were dried (MgSO4), filtered and concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (58 mg, 30%). 1H NMR (270 MHz, CDCl3): delta 1.12-1.89 (12H, m, 12 x CH), 2.03-2.16 (2H5 m, 2 x CH)3 2.40-2.46 (IH, m, CH), 2.83 (2H, ‘t’, J= 11.1 Hz, CH2), 3.15 (IH, ‘t J= 12.4 Hz, CH), 3.49-3.54 (IH, m, CH), 3.83 (IH, bd, J= 13.9 Hz, CH), 4.0 (IH, s, CH)5 4.42 (IH, d, J= 14.1 Hz, NH)5 6.60-6.66 (IH, td5 J= 1.2, 1.5, 7.8 Hz, ArH)5 6.73-6.77 (IH5 dd5 J = 1.2, 8.2 Hz, ArH), 6.78-6.82 (IH, dd, J = 1.2, 7.9 Hz, ArH), 6.84-6.91 (2H, m, ArH)5 7.00- 7.06 (IH5 td, J = 1.5, 0.8, 7.5 Hz, ArH), 7.19-7.26 ppm (2H, m, ArH). 13C NMR (67.93 MHz, CDC13): delta 26.0, 29.4, 29.6, 32.2, 33.3, 40.5, 44.1, 49.9, 112.2, 117.2, 118.8, 119.6, 125.3, 127.9, 129.8, 138.9, 143.0, 156.1, 174.6 ppm LCMS: M+H: 413.47 HPLC: 100% (retention time 3.210 min, isocratic 90% acetonitrile : 10% water, 1 ml/min).

According to the analysis of related databases, 2-(4-Chlorophenoxy)aniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

17318-08-0, The chemical industry reduces the impact on the environment during synthesis 17318-08-0, name is 5-Bromo-1,3-dichloro-2-fluorobenzene, I believe this compound will play a more active role in future production and life.

A stirred mixture of 5-bromo-1,3-dichloro-2-fluorobenzene (2.00 g, 8.20 mmol), l-methoxy-4-vinylbenzene (1.32 g, 9.80 mmol), and triethylamine (20 mL) under argon was degassed for 5 minutes. Palladium(II) acetate (0.0368 g, 0.164 mmol) and 1,1′- bis(diphenylphosphino)ferrocene (0.181 g, 0.328 mmol) were added and the reaction was heated to 90 C for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography provided the title compound as an off-white solid (1.60 g, 67%): lH NMR (300 MHz, CDCb) delta 7.41 (d, J = 8.8 Hz, 2H), 7.31 (s, 1H), 7.37 (s, 1H), 6.96 (d, J = 16.0 Hz, 1H), 6.89 (d, J = 8.8 Hz, 2H), 6.76 (d, J = 16.0 Hz, 1H), 3.84 (s, 3H); ESIMS m/z 297 ([M + H]+).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1,3-dichloro-2-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DOW AGROSCIENCES LLC; HEEMSTRA, Ronald J.; ROSS, Ronald; DEKORVER, Kyle A.; GRAY, Kaitlyn; KNUEPPEL, Daniel I.; VEDNOR, Peter; MARTIN, Timothy P.; ECKELBARGER, Joseph D.; DAEUBLE, John F.; HUNTER, Ricky; DEMETER, David A.; TRULLINGER, Tony K.; BAUM, Erich W.; BENKO, Zoltan L.; CHOY, Nakyen; CROUSE, Gary D.; LI, Fangzheng; NISSEN, Jeffrey; OLSON, Monica B.; RIENER, Michelle; SPARKS, Thomas C.; WESSELS, Frank J.; YAP, Maurice C.; (981 pag.)WO2016/168059; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 202197-26-0. 202197-26-0

Example-1 Preparation of N1-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethyl formamidine (8) Into a one liter four necked round bottomed flask, 500 mL of toluene, 50.0 g of 3-chloro-4-(3-fluoro-benzyloxy)-aniline, 50.0 g of dimethylformamide dimethyl acetal and 3.0 mL of acetic acid were charged under stirring. The reaction mixture was maintained at reflux temperature for about 2 hrs and the completion of the reaction was monitored by TLC. The solvent was completely distilled off under vacuum, the resulting syrupy liquid was cooled to room temperature. To this 200 mL of water was added and adjusted to basic pH by adding dilute sodium hydroxide solution. The product was extracted into ethylacetate and separated the organic layer. The organic layer was clarified by carbon treatment and filtered. The filtrate was completely distilled off under vacuum. The mass was cooled to room temperature and added 250 mL of hexane and stirred at 0 to 5 C. for about two hours to crystallize the product. The product was filtered and dried under vacuum at 30-35 C. to get 58.0 gram (95% by theory) of N1-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethylformamidine as a white crystalline powder. Purity: 99.66% by HPLC Melting-range: 45-47 C. Mass: 307.5 [M+1] IR (KBr, cm-1): 2917, 2798, 2364, 1637, 1591, 1557, 1500, 1453, 1410, 1373, 1269, 1250, 1205, 1137, 1103, 1059, 1016, 926, 877, 859, 809, 772, 749, 704, 680, 637, 606, 519. 1H-NMR (400 MHz; DMSO-D6): delta 2.87 (s, 3H); delta 2.98 (s, 3H); delta 5.15 (s, 2H); delta 6.80-6.83 (dd, 1H); delta 6.99-7.00 (d, 1H); delta 7.04-7.06 (d, 1H); 7.14-7.18 (m, 1H); delta 7.26-7.30 (m, 2H); delta 7.42-7.47 (m, 1H); delta 7.72 (s, 1H) 13C-NMR (400 MHz; DMSO-D6): delta 33.90 (2C), 69.56, 114.0, 115.19, 120.21, 121.51, 121.90, 123.20, 130.45, 140.02, 146.71, 148.41, 153.76, 160.97, and 163.39.

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 3-Chloro-4-((3-fluorobenzyl)oxy)aniline.

Reference:
Patent; Natco Pharma Limited; US2011/263852; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2770-11-8, Adding a certain compound to certain chemical reactions, such as: 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2770-11-8.

General procedure: A mixture of NaOH solution (2 molL-1, 20mL), 1,4-dioxane (2 mL) and compound 4 (5 mmol) was dissolved and cooled to 0 C in an ice bath. While stirring the mixture, compound 14, 15 or 16 was added slowly. Afterwards, the mixture was stirred for another 5h at room temperature. The mixture was then extracted with ethyl acetate, and the solvent was removed in vacuum. The crude product was purified by column chromatography on silica gel to give compounds 17a-17i, 18a-18i or 19a-19i in yields of 30-73%. All the compounds were list in Table1 and the spectral parameters for 1H NMR, IR and MS were as follows.

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-(4-Chlorophenoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wen, Fang; Jin, Hong; Tao, Ke; Hou, Taiping; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 244 – 251;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

33863-76-2, Adding a certain compound to certain chemical reactions, such as: 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33863-76-2.

Sodium methoxide (4.5M solution in methanol, 2.20 [ML,] 10.0 [MMOL)] was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 [MMOL)] in methanol (28 [ML)] at room temperature under a nitrogen atmosphere. The mixture was heated at reflux for 3 days and then cooled to room temperature. The mixture was evaporated under reduced pressure and the resulting yellow oil was dissolved in [DICHLOROMETHANE] (30 [ML).] The [DICHLOROMETHANE] solution was washed with water [(2X20] [ML)] dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel eluting with cyclohexane to provide the title compound as a colourless oil (302 mg). [1 H-NMR (400MHZ, CDC13)] : [8] 3.77 (s, 3H), 6.82 (s, 1 H), 6.94 (s, 1 H), 7.09 (s, [1 H).] Microanalysis : Found: C, 37.94 ; H, 2.75. [C7H6BRCIO] requires ; C, 37.96 ; H, 2.73%.

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, 1-Bromo-3-chloro-5-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, Name is 1-Bromo-4-chloro-2-fluorobenzene, 1996-29-8, 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.

Step-l: Synthesis of 3-bromo-6-chloro-2-fluorobenzaldehyde 2Reaction scheme: To a stirred solution of l-Bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added 2.0 M lithium diisopropylamide (LDA) in THF (620 mL, 1.24 mol, 1.3 equiv.) at -50 C, the reaction mixture was allowed to -20 C and stirred for 1 h. Then it was re-cooled to -50 C and slowly added DMF (184.8 mL,2.48 mol, 2.6 equiv.) at the same temperature. The mixture was allowed to 0 C and stirred for 30-45 min. After completion of the reaction (monitored by TLC), it was quenched with the slow addition of ice cold water (2.0 L); then diluted with ethyl acetate (2.0 L) and stirred for 15 min at room temperature. The organic layer was separated and aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HC1 (1.0 L) and.5% NaCl solution (2.0 L). The organic layer was dried over anhydrous NaiSOr. concentrated under vacuum. The resultant crude solid was directly used for next step without further purification. Yield: 210.0 g, 93% (reported 78%). NMR (400 MHz, CDCb): d 10.39 (d, J= 0.8 Hz, 1H), 7.69 (dd, Ji = 7.2 Hz, J2 = 8.8 Hz, 1H), 7.19 (dd, Ji = 1.2 Hz, J2 = 8.4 Hz, 1H).

Statistics shows that 1-Bromo-4-chloro-2-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1996-29-8.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BENDER, John A.; FRENNESSON, David B.; GILLIS, Eric P; IWUAGWU, Christiana; KADOW, John F; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M.; RAJAMANI, Ramkumar; SAULNIER, Mark G.; WANG, Alan Xiangdong; (313 pag.)WO2019/198024; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, 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. 27139-97-5

To a solution of 2-bromo-4-chloro-l-methylbenzene (25 g, 0.123 mol) in anhydrous THF (150 mL) at -78 0C under N2 was added drop wise a solution of n- BuLi (2.5 M, 49 mL, 1.18 mol). After stirring at -78 0C for 1 h, a solution of tert- butyl 3-(5-chloro-2-methylphenyl)-3-oxopropyl(methyl)carbamate (26 g, 0.104 mol) in anhydrous THF (150 mL) was added drop wise. After addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with saturated NH4Cl, extracted three times with ethyl acetate, and dried over Na2SO4. Solvent removal and flash column chromatography afford tert-butyl 3-(5-chloro-2-methylphenyl)-3-oxopropyl(methyl)carbamate (3.3 g, yield 9 percent). 1H NMR (CDCl3, 400 MH2) delta 1.44 (s, 9H), 2.45 (s, 3H), 2.90 (s, 3H), 3.10 (m, 2H), 3.60 (m, 2H), 7.10 (m, 3H).

Statistics shows that 27139-97-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-4-chloro-1-methylbenzene.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2008/156816; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics