Chlorides-buliding-blocks

2533-69-9, These common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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.

Methyl 2,2,2-trichloroacetimidate (408 ml, 3.30 mmol), diisopropylethylamine (473 ml, 2.72 mmol) and ammonium chloride (73 mg, 1.36 mmol) were added to a solution of compound 96 (943 mg, 3.00 mmol) in acetic acid (6.0 ml) under ice-cooling, and the mixture was stirred for 45 minutes at room temperature. After water (15 ml) was added to the reaction mixture, precipitated crystals were collected and dissolved in THF (27 ml). 5 N sodium hydroxide solution (3 ml) was added to the solution and the mixture was stirred for 1 .5 hours at room temperature. The reaction mixture was concentrated and acidified to pH 3 – 4 with 2 N hydrochloric acid. Precipitated crystals were collected and washed with water to give compound 99 (770 mg, 70 %) as reddish-brown crystals. NMR (CDCl3) ?: 4.28 (3H, s), 4.45 (2H; s), 7.06 (2H, m), 7:33-(1H; d; J=8.5Hz), 7.39 (2H, m), 7.80 (1H, d, J = 8.6 Hz).

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 2533-69-9.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1375486; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 344-19-4 as follows. 344-19-4

Method 2: Example 27: [2-(2,6-Dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)amine Step 1 : l-(4-Azidopyridin-3-yl)meth-(E)-ylidene]-(2,6-dichloro-4-fluorophenyl)amine Titanium tetrachloride (1M, 4.0 mL, 4.15 mmol) was added to a cooled (0 C) mixture of 4-azidopyridine-3- carbaldehyde (1.0 g, 6.75 mmol), 2,6-dichloro-4-fluorophenylamine (1.22 g, 6.75 mmol) and triethylamine (2.8 mL, 20.3 mmol) in DCM (24 mL), under nitrogen. The reaction was stirred for 30 minutes at 0 C, warmed to room temperature, stirred for an additional 2 h, and concentrated under reduced pressure. The residue was dissolved in toluene and filtered though a pad of Celite. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (2.09 g, quant.). This crude material was employed in the next step without further purification or analysis.

According to the analysis of related databases, 344-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; GOODACRE, Simon; LAI, Yingjie; LIANG, Yun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/66061; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-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. 823-57-4

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous bromide (0.02 mmol), 2-bromo-5-chloroaniline (0.4 mmol),1,10-azaphenanthroline (0.04 mmol), pyridine (0.4 mmol),Carbon disulfide (0.4 mmol), NMP (2.0 mL), was added with a syringe under oxygen.The reaction tube was placed in a 130 C oil bath for 10 hours.The resulting solution was cooled to room temperature, and 2 mL of deionized water was added to the reaction solution.Mix well, each time with 3mL of ethyl acetate as extractant through liquid separation extraction operation,The crude product is extracted from the reaction solution, and the extract is combined.And removing the solvent by a rotary evaporator;The residue was purified on a silica gel column (silica gel size 200 mesh to 300 mesh,The eluent is petroleum ether/ethyl acetate (15:1 v/v),The target product was obtained in 69.1 mg, yield 82%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 823-57-4, its application will become more common.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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