Month: November 2020

A common heterocyclic compound, 452-73-3, name is 2-Chloro-4-fluoro-1-methylbenzene, molecular formula is C7H6ClF, 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. 452-73-3.

A mixture of 77.6 g (0.54 mol) of 2-chloro-4-fluorotoluene, 95.6 g(0.54 mol) of N-bromosuccinimide, 1 g of benzoyl peroxide, and 1000 ml of carbon tetrachloride were refluxed for 3 h. The resulting mixture was cooled to room temperature and then filtered through a glass frit (G3). The precipitate was additionally washed with 3 x 100 ml of carbon tetrachloride. The combined filtrate was evaporated to dryness. Fractional distillation of the residue gave pure title product, bp 97-99C/10 mm Hg. Yield 106 g (88%).Anal. calc. for C7H5BrClF: C, 37.62 H, 2.26 Found: C, 37.79; H, 2.34.1H NMR (CDCl3): delta 7.41 (dd, J=8.4 Hz, J=6.0 Hz, IH, 6-H), 7.13 (dd, J=8.4 Hz, J=2.6 Hz, IH, 3-H), 6.97 (dt, J=8.4 Hz, J=2.6 Hz, IH, 5-H), 4.55 (s, 2H, CH2).

The synthetic route of 2-Chloro-4-fluoro-1-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS INC.; WO2007/70041; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

445-14-7,Some common heterocyclic compound, 445-14-7, name is 2-Amino-4-chlorobenzotrifluoride, molecular formula is C7H5ClF3N, 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 5 3-((5-chloro-2-(trifluoromethyl)phenyl)ethvnyl)-5-(l-(piperidin-4-yl)-lH-pyrazol-4- yl)-lH-pyrrolor2,3-b1pyridine Step 1) 2-bromo-4-chloro-l-(trifluoromethyl)benzene To a stirred solution of 40percent HBr (2.20 mL, 15.34 mmol) in 0 (2 mL) was added 2-amino-4- chlorobenzotrifluoride (0.50 g, 2.56 mmol) at 0 ¡ãC. Then a solution of sodium nitrite (0.21 g, 3.07 mmol) in H20 (2 mL) was added dropwise at 0 ¡ãC. The mixture was stirred at 0 ¡ãC for a further 0.5 hours, a solution of cuprous bromide (0.63 g, 4.35 mmol) in 40percent HBr (2.20 mL, 15.34 mmol) and H20 (3 mL) was added. The mixture was stirred at 75 ¡ãC for 3 hours, then cooled to rt, and extracted with EtOAc (40 mL x 4). The combined organic phases were washed with brine (80 mL x 2), dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound as a yellow liquid (0.76 g, 100percent). GC -MS: 257.9.

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

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Xiaobo; ZHOU, Shiqing; WO2014/89280; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

96558-78-0,Some common heterocyclic compound, 96558-78-0, name is 3-Bromo-5-chlorophenylamine, 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.

(S)-tert-Butyl l-(3-bromo-5-chlorophenylamino)-l-oxo-3-phenylpropan-2-ylcarbamate (46.D). 3-bromo-5-chlorobenzenamine (3.73 g, 18 mmol) and (S)-2-(tert- butoxycarbonyl)-3-phenylpropanoic acid (4.8g, 18 mmol) were dissolved in DMF (100 mL, 1291 mmol) then triethylmine (5 mL, 36 mmol) and HBTU (14 g, 36 mmol) were added and the mixture was stirred for 14 h. After 14 hours the reaction was diluted with 500 mL EtOAc and the organic was washed with IN HCl and saturated bicarbonate solution. The extract was concentrated under reduced pressure on a rotary evaporator to afford a residue. The residue was purified on silica eluting with EtO Ac/Hex in a linear gradient.

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

Reference:
Patent; AMGEN INC.; DU, Xiaohui; FU, Zice; HOUZE, Jonathan, B.; JIAO, Xianyun; KIM, Yong-jae; LI, Leping; LIU, Jinqian; LIZARZABURU, Mike; MEDINA, Julio; SHEN, Wang; TURCOTTE, Simon; YU, Ming; WO2010/93849; (2010); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 627-42-9 name is 2-Methoxyethyl chloride, 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. 627-42-9

General procedure: The 7-alkoxy-1-methyl-beta-carbolines (3a-o) were synthesized according to a previously reported procedure.13 The appropriate alkyl halide (by portion) or 1-tosyl-4,4,4-trifluorobutane (for compound 3e) and cesium carbonate were added to harmol (2) dissolved in anhydrous dimethylformamide (DMF). Then, the reaction mixture was stirred at room temperature or heated for several hours. At the end of the reaction, the mixture was cooled and diluted with dichloromethane, washed once with water and three times with brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by liquid chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methoxyethyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Reniers; Robert; Frederick; Masereel; Vincent; Wouters; Bioorganic and Medicinal Chemistry; vol. 19; 1; (2011); p. 134 – 144;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

823-57-4, 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 823-57-4 as follows.

A 10 L round-bottom flask was charged with 200 g (1.64 mol, 1.05 eq.) of Phenylboronic acid, 322 g (1.56 mol, 1 eq.) of 2-bromo-5-chloroaniline, 90 g (78.10 mmol, 0.05 eq.) of Pd(PPh3)4, and 646 g (4.69 mol, 3 eq.) of K2CO3, after which toluene/EtOH/H2O was added thereto, and the mixture was stirred under reflux. After completion of the reaction, the mixture was extracted with MC/H2O and the MC layer was dried over MgSO4. Purification was performed using a silica-gel column to obtain 254 g of Core 1-1 at a yield of 80percent.

According to the analysis of related databases, 2-Bromo-5-chloroaniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOULBRAIN CO., LTD.; HA, Jong Jin; YOO, Hyun Young; KIM, Sung Soo; LEE, Seok Jong; (103 pag.)US2019/161485; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

95-51-2, Adding some certain compound to certain chemical reactions, such as: 95-51-2, name is 2-Chloroaniline, 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 95-51-2.

To a solution of 2-chloro aniline (26 g, 0.204 mol.) in THF (260 mL) was added butyl lithium (2.5 M, 80 mL, 0.2 mol) at -5O0C. The reaction was stirred at -50C for 0.5 hours then allowed to reach room temperature. After 0.5 hours at room temperature, the mixture was cooled to -500C then iodomethane (12.4 mL, 0.2 mol.) was added. After stirring at -500C for 0.5 hours, the mixture was warmed up to room temperature and stirred for 5 hours. The mixture was poured in saturated NH4CI solution then the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water then dried on sodium sulphate. After filtration and evaporation to dryness, the residue was purified by flash column chromatography eluting with EtOAc/petroleum ether: 1/100 to give the title compound as a clear oil (12 g, 42%). 1H NMR (300 MHz, DMSO, ppm) delta: 7.21 (d, 1 H), 7.13 (t, 1 H), 6.50 (m, 2H), 5.45 (bs, 1 H), 2.72 (d, 3H).

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 95-51-2.

Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, Adding a certain compound to certain chemical reactions, such as: 1996-29-8, name is 1-Bromo-4-chloro-2-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 1996-29-8.

A 2 L round bottom flask was charged with 1-bromo-4-chloro-2-fluorobenzene(1-bromo-4-chloro-2-fluorobenzene, 50 g, 238.7 mmol)And anhydrous tetrahydrofuran 900 ml was added and the mixture was cooled to -78C with stirring.N-butyl lithium (2.5 M hexane solution; 100 ml, 250 mmol)And the mixture was stirred for 1 hour.Trimethylborate (31.9 ml, 286 mmol) was slowly added thereto,After 30 minutes, 600 ml of a 1N hydrogen chloride aqueous solution was addedThe temperature was raised to room temperature while stirring.The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The mixture was distilled under reduced pressure, concentrated, and extracted with chloroform and hexaneAnd recrystallized to obtain Compound 1 (33.7 g, 193.3 mmol) in a yield of 81%.

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

Reference:
Patent; LG Chemical Co., Ltd.; Hong, Sung Gil; Kim, Yeon Hwan; Kim, Sung So; Ho, Jung Oh; Cho, Sung Mi; Kim, Hyung Suk; (37 pag.)KR101680413; (2016); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 2533-69-9.

[00748] To a solution of 4-chloro-5-(4-chlorobenzyloxy)benzene-1,2-diamine (282 mg, 1 mmol) in DCM (4 mL) and ethyl ether (1.6 mL) at 0C was added methyl 2,2,2-trichloroacetimidate (260 mg, 1.5 mmol) and TFA (1.6 mL). The resulting reaction mixture was stirred at 15C for 20 h. The reaction was quenched by adding ice, and white solid was formed, and then filtered. The solid was washed with excess DCM. The filtrate was concentrated in vacuo at 20C to give the residue (200 mg) as a tan gum,. The residue was used directly in the next step. ESI-MS (EI+, m/z):

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; MAHONEY, Sarah; MOLZ, Lisa; NARAYAN, Sridhar; SAIAH, Eddine; (516 pag.)WO2018/191146; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

96558-78-0, These common heterocyclic compound, 96558-78-0, name is 3-Bromo-5-chlorophenylamine, 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.

3-chloro-5-bromoaniline (1 g, 4.84 mmol) was dissolv ed in 75% I LSO ( 10 mL). Then glycerol (1.1 1 g, 12.1 mmol ) and nitrobenzene (0.59 g. 4.84 mmol ) were added. The reaction mixture was stirred at 150C for 3 hours under N2. EtOAc (50 ml ) was added and the mixture was adjusted to pH to 6-7 with a 30% solution of NaOH in water. The solid was filtered off over celite and the organic layer was separated and ev aporated. The residue was purified by flash column chromatograph over silica gel (gradient eiuent: petroleum ether EtOAc from 20/ 1 to 5/1). The desired fractions were collected and the solvent was evaporated to give a mixture of intermediate 457 and intermediate 458 (750 mg) as a white solid.

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 96558-78-0.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 2453-46-5, name is Chlorocycloheptane, 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 2453-46-5. 2453-46-5

A 1.64 M THF solution of phenylmagnesium chloride (1.10 mL, 2.40 mmol) was added at 0 C. to 0.6 mL of a THF solution of aluminum chloride AlCl3 (80.0 mg, 0.60 mmol). The reaction mixture was stirred at room temperature for 1 hour. To the resulting solution was added 1,2-bis(bis(3,5-di-tert-butylphenyl)phosphino)benzene ([3,5-(t-Bu)2]-DPPBz) (13.4 mg, 0.015 mmol) and a 0.1 M THF solution of iron chloride FeCl3 (0.15 mL, 0.015 mmol) at 0 C., followed by chlorocycloheptane (66.3 mg, 0.5 mmol). The coupling reaction was performed at 80 C. for 24 hours. After cooling to room temperature, a portion of the reaction mixture was taken out, and the yield of the product was measured by gas chromatography (GC), using undecane as an internal standard. The yield was 94%. The results are shown in the Entry 5 column of Table 8.

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 Chlorocycloheptane.

Reference:
Patent; Kyoto University; US2011/152523; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics