Tag: M.W=200-300

60811-21-4,Some common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, molecular formula is C6H3BrClF, 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 dissoprppylamine (5.1 mL, 36.0 mmol, 1.5 eq.) in anhydrous THF (15 mL) was added n-BuLi (19.2 mL, 28.8 mmol, 1.2eq.) dropwise at -78C under N2 atmosphere, then was added the 4-bromo-2-chloro-l-fluorobenzene (5 g, 24.0 mmol, 1.0 eq.) at -78C 1 h later. The mixture was stirred at -78C for 45 minutes, then was added DMF (2.8 mL, 36.0 mmol, 1.5 eq. ), warmed to -30C until TLC showed that the reaction was completed. The reaction was quenched with H20 (100 mL), then adjusted to pH 2-3, extracted with EA (50 mLx3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and evaporated. The residue was purified by column chromatography (PE/EA=100: 1) to provide 5-bromo-3-chloro-2-fluoroben low solid.

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

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (297 pag.)WO2018/229543; (2018); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

Preparation 5 TERT-BUTYL 3-(3-CHLORO-5-FLUOROPHENYL)-3-HYDROXYPYRROLIDIN-1-CARBOXYLATE To a solution of 1-bromo-3-chloro-5-fluorobenzene (4.0 g, 19.1 mmol) in dry tetrahydrofuran (40 mL), under nitrogen, was added magnesium turnings (0.47 g, 21.0 mmol) and a small piece of iodine. The mixture was heated with a heat-gun until the colour disappeared and then stirred at ambient temperature for 0.5 h after which a solution of 1-N-boc-3-pyrrolidinone (2.8 g, 15.3 mmol) in dry tetrahydrofuran (10 mL) was added drop wise. The reaction mixture was stirred for 0.5 h at ambient temperature and then quenched with water (70 mL). Aqueous saturated ammonium chloride (20 mL) was added and the mixture was extracted with ethyl acetate (2*100 mL). The combined organic phase was dried (MgSO4), filtered and evaporated. Purification by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:1) gave the title compound (2.43 g). MS m/z (rel. intensity, 70 eV) 315 (M+, 1), 259 (14), 214 (22), 184 (13), 143 (11), 57 (bp).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB; US2010/179211; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 63624-28-2, 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. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 24:Methyl 3-(5-(4-(2,4-dimethoxyphenylsulfonamido)phenyl)thiazol-2-yl) propanoate The compound of example 5 (100 mg) was dissolved in methylene chloride (2 mL) to which pyridine (0.061 mL) was added and the reaction mixture was stirred for 5 min. To this reaction mixture, 2,4-dimethoxybenzene-1 -sulfonyl chloride (0.135 g) was added and the reaction mixture was stirred for 16 h. Water was added into the reaction mixture and the reaction mixture was neutralized with dilute hydrochloric acid. The organic layer was washed with water and dried over anhydrous Na2S04. The solvent was evaporated to obtain an oil, which was purified by column chromatography (silicagel, EtOAc in chloroform) to obtain a solid, which was crystallized using EtOAc in petroleum ether to afford the title compound. Yield: 153 (86 %); 1H NMR (DMSO-d6, 300MHz): delta 10.07 (s, 1 H), 7.88 (s, 1 H), 7.71 (d, 1 H), 7.44 (d, 2H), 7.12 (d, 2H), 6.63 (d, 1 H), 6.57 (dd, 1 H), 3.86 (s, 3H), 3.78 (s, 3H), 3.59 (s, 3H), 3.22 (t, 2H), 2.79 (t, 2H); MS: m/z 463 (M+1 ).

The synthetic route of 2,4-Dimethoxybenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; SHARMA, Rajiv; KADAM, Kishorkumar Shivajirao; JADHAV, Ravindra Dnyandev; KANDRE, Shivaji Sadashiv; GUPTE, Amol; WO2012/29032; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 883499-24-9, 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. 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

5.3) 1-Benzylsulfanyl-3-bromo-2-chloro-benzene (intermediate 16): To stirred phenyl-methanethiol (14.8 g, 119,36 mmol) in 175 ml DMF was added Cs2CO3 (38.89 g, 119.36 mmol) under argon. After 10 min 1-bromo-2-chloro-3-fluoro- benzene (25 g, 119.36 mmol) in 25 ml DMF was added and stirring was continued overnight at RT and then 3 h at 800C. After cooling the mixture was diluted with ethyl acetate/water and washed subsequently with 1 N HCI and brine. The organic layer was dried with MgSO4, filtered and evaporated. Purification by chromatography on silica gel yielded 22 g (59 %) as an amorphous, colourless solid.

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

Reference:
Patent; SANOFI-AVENTIS; WO2009/103440; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 41965-95-1, 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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

9-((3-chloro-4-methoxybenzyl)amino)-2-ethyl-7-methoxy-2,3-dihydro-lH- pyrrolo[3,4-b]quinolin-l-one L [00289] A solution of 43 (0.11 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (0.16 mmol) and (‘pr)2NEt (0.66 mmol) in n-propanol (1.5 mL) was heated to 90 C for lh. The solvent was evaporated off and the residue was purified by flash chromatography (AcOEt: MeOH 19: 1) to give the final product L. MS ESI (m/z) 412 (M+H)+; 1H NMR (400 MHz, CDC13) delta 8.14 (t, 1H, J=6.4 Hz), 7.85 (d, 1H, J=9.6 Hz), 7.48 (d, 1H, J=2.4 Hz), 7.37-7.29 (m, 3H), 6.95 (d, 1H, J=8.8 Hz), 4.95 (d, 2H, J=6.8 Hz), 4.38 (s, 2H), 3.90 (s, 3H), 3.66 (q, 2H, J=7.2 Hz), 3.59 (s, 3H), 1.28 (t, 3H, J=7.2 Hz)

The synthetic route of 3-Chloro-4-methoxybenzylamine Hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1127-85-1, A common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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 NaOH (79.2 mg, 1.98 mmol) in 90% aqueous methanol solution (1.8 mL)A solution of thiophenol (193 muL, 1.89 mmol) in methanol (2.9 mL) was slowly added dropwise at 0 C., The mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (350 mg, 1.72 mmol) in methanol (2.9 mL) was slowly added dropwise at 0 C,The mixture was stirred at room temperature for one day.After completion of the reaction was confirmed by TLC,After diluting with ethyl acetate,And extracted with brine. The organic layer was dried over anhydrous Na2SO4,Filtered and concentrated. The concentrated filtrate was separated and purified by silica gel column chromatography (Hex: EtOAc = 20: 1) to obtain the desired compound (475 mg, 99%) as a white solid.

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; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; Nam, Ghil-Soo; Choo, Hyun-Ah; Choi, Kyung-Il; (40 pag.)KR101730790; (2017); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 873-38-1, name is 2-Bromo-4-chloroaniline, molecular formula is C6H5BrClN, 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. SDS of cas: 873-38-1

A mixture of 2-bromo-4-chloroaniline (4g), sodium carbonate (6.Ig) phenylboronic acid (2.93g) and tetrakis(triphenylphosphine)palladium(0) (0.5g) in dioxane (30ml) was heated under reflux for 48h then cooled. The mixture was partitioned between ethyl acetate and water, the organic layer was washed with water, dried, and the solvent evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-10% ethyl acetate/isohexane, yield 0.99g. MS: APCI (+ve) 204/6

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 873-38-1, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/37982; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 467435-07-0, These common heterocyclic compound, 467435-07-0, name is 4-Bromo-2-chlorobenzotrifluoride, 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.

Example 1677 Production of (4aS,8aS)-3,3-dimethyl-l-(3-chloro-4-trifluoromethylphenyl)decahydroquinoxali ne dihydrochloride n A toluene (5 mL) suspension of (4aS,8aS)-2,2-dimethyldecahydroquinoxaline (200 mg, 1.19 mmol), 4-bromo-2-chloro-l-trifluoromethylbenzene (370 mg, 1.43 mmol), sodium tert-butoxide (137 mg, 1.43 mmol), palladium (II) acetate (21.3 mg, 0.0951 mmol), and tri-tert- butylphosphine tetrafluoroborate (27.6 mg, 0.0951 mmol) was stirred for 4 hours at 100 C in a nitrogen atmosphere. After the reaction mixture was cooled to room temperature, insoluble matter was filtered through celite, and the filtrate was then concentrated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (n-hexane: ethyl acetate) to obtain pale yellow oil. 1 N hydrochloric acid/ethyl acetate (5.0 mL) was added to an ethanol solution of the obtained oil with stirring at room temperature, and, after sufficient stirring, the mixed solution was concentrated under reduced pressure. The obtained oil was added with an appropriate amount of ethanol/ethyl acetate and the deposited crystal was collected by filtration. The obtained crystal was washed with ethyl acetate and then dried under reduced pressure to obtain (4aS,8aS)-3,3-dimethyl-l-(3-chloro-4- trifluoromethylphenyl)decahydroquinoxaline dihydrochloride (348 mg, yield: 70%) in a white powder form.

The synthetic route of 467435-07-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; SHINOHARA, Tomoichi; SASAKI, Hirofumi; TAI, Kuninori; ITO, Nobuaki; WO2013/137479; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 38762-41-3, 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. 38762-41-3, name is 4-Bromo-2-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A degassed solution of 3-trifluoromethanesulfonyloxy-furo[3,2-c]pyridine-2- carboxylic acid ethyl ester (300 mg, 0.88 mmol), 4-bromo-2-fluoro aniline (201 mg, 0.97 mmol), Pd2dba3 (40 mg, 0.044 mmol), Xantphos (59 mg, 0.044 mmol) and potassium phosphate tribasic (373 mg, 1.76 mmol) in toluene (5 ml) was heated at reflux under an argon atmosphere for 16 hours. The reaction mixture was filtered and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si-SPE, pentane: diethyl ether, gradient 80:20 to 50:50) to afford the title compound as a yellow solid (177 mg, 51%). LCMS (method B): Rx = 3.76 min, M+H+ = 395 / 397.

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-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 98577-44-7, A common heterocyclic compound, 98577-44-7, name is 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane, molecular formula is C5H6Br2Cl2, 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.

Step 1 : A flame-dried pressure tube was charged with l,l-dibromo-2,2- bis(chloromethyl)cyclopropane (15 g, 50.5 mmol) and dibutyl ether (15 mL). The reaction was cooled to -45 C and PhLi (53.2 mL, 101 mmol, 1.8M in dibutyl ether) was added slowly via syringe. The mixture was stirred at the same temperature for 5 mins. The reaction temperature was allowed to warm to 0 C and stirred for 2 h in an ice bath at which point the reaction was brought to RT to provide a solution of crude [l. l. l]propellane.

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; KALYRA PHARMACEUTICALS, INC.; BUNKER, Kevin, Duane; HUANG, Peter, Qinhua; ABRAHAM, Sunny; PINCHMAN, Joseph, Robert; HOPKINS, Chad, Daniel; SLEE, Deborah, Helen; (93 pag.)WO2017/205459; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics