Category: chlorides-buliding-blocks

Application of 771583-81-4, These common heterocyclic compound, 771583-81-4, name is 4-Chloro-2-(trifluoromethyl)benzylamine, 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.

5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2-fluorobenzoic acid (150.0 mg, 0.4 mmol), HATU (234.0 mg, 0.6 mmol), and DIPEA (211.8 mg, 1.6 mmol) ) Dissolved in tetrahydrofuran (10mL), stirred at room temperature for 0.5 hours, then added 4-chloro-2- (trifluoromethyl) benzylamine (129.1mg, 0.6mmol), reacted at room temperature for 4 hours, then added an appropriate amount Water and extracted three times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (100.0 mg, yield: 42%).

The synthetic route of 771583-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Chunchi; Liu Jinming; Ren Yun; Cai Jiaqiang; Wang Lichun; Wang Jingyi; (42 pag.)CN110724075; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2106-02-7, 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. 2106-02-7, name is 2-Chloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Lithium hexamethyldisilazide (22.9 ml, 22.9 mmol, 1 M solution in tetrahydrofuran) was added over 5 min to solution of 2-chloro-4-fluoroaniline (1 .84 g, 12.6 mmol, Cas No 2106-02-7) in tetrahydrofuran (60 ml) at -78 and the mixture was stired at -78 for 1 h. A solution of ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate (mixture of cis-/trans-isomers) (4.00 g, 1 1 .5 mmol) in tetrahydrofuran (60 ml) was added and the mixture was stirred for 2 h at -78 and the for 3 days at room temperature. For work-up, the reaction mixture was poured into a mixture of water and saturated sodium bicarbonate solution, extracteted with ethyl acetate (3x) and the combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressured. The residue was purified by flash chromatography (Snap Cartdidge, hexanes/ethyl acetate gradient) to give 8-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-chloro-4-f luorophenyl)-2-azaspiro[4.5]decan-1-one in 2 fractions. Fraction 1 (1 .88 g, isomer 1, contains ca 20mol% 2-chloro-4-fluoroaniline) and fraction 2 (485 mg, isomer 2).Fraction 1 (isomer 1 ):LC-MS (Method 1 ): Rt= 1 .68 min; MS (ESIpos) m/z = 412.2 [M+H]+.1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.58 (dd, 1H), 7.46 (dd, 1H), 7.30 (td, 1H), 3.97-3.92 (m, 1H), 3.59 (t, 2H), 2.06 (t, 2H), 2.01-1 .92 (m, 2H), 1.71-1.54 (m, 4H), 1 .36-1 .29 (m, 2H), 0.92-0.86 (m, 9H), 0.08-0.03 (m, 6H).Fraction 2 (isomer 2):LC-MS (Method 1 ): Rt= 1 .67 min; MS (ESIpos) m/z = 412.2 [M+H]+.1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.57 (dd, 1H), 7.45 (dd, 1H), 7.33-7.25 (m, 1H), 3.70-3.52 (m, 3H), 2.07 (t, 2H), 1 .84-1 .74 (m, 2H), 1.62-1 .54 (m, 4H), 1 .42-1.28 (m, 2H), 0.89-0.83 (m, 9H), 0.07-0.01 (m, 6H)

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, A new synthetic method of this compound is introduced below., Product Details of 13078-79-0

General procedure: NaBH(OAc)3 (3 eq) was added to an ethanol solution (15 mL)of the aldehyde 9 (1 g) and alkylamines (2 eq), and the mixture was stirred for 4 h at 0 to room temperature. After completionof the reaction, the reaction mixture was evaporated under reduced pressure to give a crude residue, which was purified by asilica gel (300-400 mesh) column using petroleum ether/ethyl acetate (5:1?2:1) to obtain pure compound 10a-i.

The synthetic route of 13078-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Haibo; Pan, Yang; Tang, Qin; Zou, Wei; Shao, Huawu; Chinese Chemical Letters; vol. 29; 1; (2018); p. 73 – 75;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2106-04-9, name is 3-Chloro-2-fluoroaniline, 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. Product Details of 2106-04-9

To a mixture of 3-chloro-2-fluoroaniline (18.0 g, 124 mmol) in MeCN (100 mL) was added a solution of NBS (26.4 g, 148 mmol) in MeCN (100 mL) in a dropwise manner at 25 C. The mixture was stirred at 25 C for 4 h. The reaction mixture was concentrated in vacuo to give the crude product. The crude material was purified by silica-gel column chromatography (petroleum ether/EtOAc, 50:1) to give 4-bromo-3-chloro-2-fluoroaniline as a brown oil (18.0 g, yield: 65%). 1H NMR: (400 MHz, CD3OD) d: 7.13 (dd, J2 = 8.8 Hz, J2 = 2.0 Hz, 1H), 6.66 (t, / = 8.4 Hz, 1H).

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; SCHULZ, Juergen; NEVALAINEN, Marta; DECHANTSREITER, Michael; (273 pag.)WO2019/222101; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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. category: chlorides-buliding-blocks

Triethylamine (51.0 g) was added dropwise to a solution of di-tert-butyl dicarbonate (100.0 g) and 3-chloropropylamine hydrochloride (71.5 g) in methanol (400 mL) at 0 C., and the mixture was then stirred at the same temperature for 16 hours. Thereafter, toluene (400 mL) and water (400 mL) were added to the reaction solution for liquid separation, and the organic layer was then washed with water. 400 mL of toluene was added to the organic layer, and the mixed solution was concentrated to 300 mL under reduced pressure. After that, N,N-dimethylacetamide (210 mL) was added, and the mixed solution was concentrated to 300 mL under reduced pressure. Thereafter, to this solution, potassium carbonate (126.66 g), tetrabutylammonium bromide (44.32 g), dimethyl malonate (90.82 g) and N,N-dimethylacetamide (100 mL) were added, and the mixed solution was then stirred at 55 C. for 20 hours. Thereafter, toluene (400 mL) and water (700 mL) were added to the reaction solution for liquid separation. The organic layer was successively washed with water, a 1 M aqueous sodium hydroxide solution and water, and was then concentrated to 150 mL under reduced pressure. To this solution, methanol (1870 mL) and a 1 M aqueous sodium hydroxide solution (430.8 mL) were added, and the mixed solution was then stirred at 0 C. for 27.5 hours. Subsequently, concentrated hydrochloric acid (2.5 mL) was added to the reaction solution, so that the pH of the solution was adjusted to pH 7-9, and the solution was then concentrated to 375 mL under reduced pressure. Ethyl acetate (500 mL) was added to the reaction solution, and concentrated hydrochloric acid (35.1 mL) was then added to the mixed solution, so that the pH of the solution was adjusted to pH 2.2-2.5, followed by liquid separation. The water layer was extracted with ethyl acetate (500 mL), the organic layer was then mixed therewith. The mixed solution was dehydrated and concentrated under reduced pressure to prepare an ethyl acetate (250 mL) solution. To the obtained solution, ethyl acetate (500 mL) and morpholine (37.5 g) were added, and the obtained mixture was stirred overnight. Thereafter, the precipitated crystals were filtrated, were then washed with ethyl acetate, and were then dried under reduced pressure to obtain the title compound (136.1 g, yield: 81.9%). (0118) 1H-NMR (DMSO-d6) delta: 6.79 (1H, t, J=5.5 Hz), 3.61 (4H, t, J=4.9 Hz), 3.58 (3H, s), 3.14 (1H, t, J=7.8 Hz), 2.90-2.80 (6H, m), 1.74-1.59 (2H, m), 1.37 (9H, s), 1.34-1.25 (2H, m) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6276-54-6, its application will become more common.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; HAYASHI, Masaki; UKAI, Kazutoshi; (16 pag.)US2018/29993; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 50638-46-5,Some common heterocyclic compound, 50638-46-5, name is 4-Bromo-3-chloroanisole, molecular formula is C7H6BrClO, 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: Preparation of 4-hydroxy-1-(2-chloro-4-methoxyphenyl)-2-methylbutan-1-one [0064] To a 1.0 L, 3-neck round bottom flask, equipped with a mechanical stirrer and an internal thermometer, was added a solution of 4-bromo-3-chloroanisole (12.0 g, 54.0 mmol) in 350 mL of THF under nitrogen. The solution was cooled to -85 C. with a MeOH/liquid nitrogen bath. To this solution was added t-BuLi (72.0 mL, 1.6 M in pentane, 122 mmol) slowly followed by the addition of a solution of alpha-methyl-gamma-butyrolactone (9.25 g, 92.0 mmol) in THF (30.0 mL). The internal temperature was controlled <-80 C. After 1 h stirring at <-80 C., the reaction mixture was quenched with saturated NH4Cl solution and warmed to room temperature. Water and EtOAc were added and separated. The aqueous layer was extracted with EtOAc (2×). The combined organic solutions was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (E:H, 1:3) to give 10.4 g (79%) of brown oil as the title compound: 1H NMR (400 MHz, CDCl3) delta 7.53 (d, J =8.6 Hz, 1H), 6.97 (d, J =2.4 Hz, 1H), 6.85 (dd, J =8.6, 2.4 Hz, 1H), 3.88 (s, 3H), 3.77-3.69 (m, 2H), 3.64-3.56 (m, 1H), 2.16-2.07 (m, 1H), 1.76-1.67 (m, 1H), 1.23 (d, J=7.0 Hz, 3H); MS (El m/z 241.16 (M+-H). 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-3-chloroanisole, its application will become more common. Reference:
Patent; Pfizer Inc; US2004/204415; (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 622-86-6 as follows. Safety of (2-Chloroethoxy)benzene

a. Diethyl 2,2-di(2-phenoxyethyl)malonate To a stirred solution of sodium (2.3 g) in absolute EtOH (50 ml) was added diethyl malonate (15.2 ml) followed by 2-phenoxyethyl chloride (15. 7 g). The reaction mixture was then refluxed for 12 hr. The EtOH was evaporated under vacuum and the mixture diluted with water (40 ml). The aqueous phase was extracted with Et2 O. The combined Et2 O extracts were washed (brine), dried (MgSO4) filtered and evaporated. Bulb to bulb distillation afforded 12.2 g (27%) of the title diester as a clear liquid, bp 155-175 (106 Pascals, 0.8 Torr); TLC, Rf =0.34, CH2 Cl2.

According to the analysis of related databases, 622-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ICI Americas Inc.; US4910190; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4, A common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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.

Intermediate 2 3-(1-Benzofur-2-yl)-6-chloroimidazo[1,2-b]pyridazine 13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1,2-b]pyridazine were suspended in 508 mL 1,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(triphenylphosphino)palladium-(0) and 90 mL (180 mmol) of a 2M aqueous sodium carbonate solution were added. The obtained mixture was heated to 100 C. for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300 MHz, DMSO-d6): delta [ppm]=7.23-7.40 (2H), 7.51 (1H), 7.59-7.67 (2H), 7.77 (1H), 8.33-8.40 (2H). LCMS (Method 1): Rt=1.35 min; MS (ESIpos) m/z=270 [M+H]+.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Eis, Knut; Puehler, Florian; Zorn, Ludwig; Schulze, Volker; Suelzle, Detlev; Lienau, Philip; Haegebarth, Andrea; Petersen, Kirstin; Boemer, Ulf; US2015/87631; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 326-64-7, 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. 326-64-7, name is 5-Chloro-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-chloro-2-(trifluoromethoxy)aniline (1.00 g, 4.73 mmol) in acetonitrile (60 mL) and water (6 mL) was added copper(II) bromide (1.48 g, 6.62 mmol). And isopentyl nitrite (0.95 g, 8.13 mmol). The mixture was stirred at 70C for 1 h. It was cooled to rt and quenched with water (200 mL). The mixture was extracted with DCM (60 mL x 2). The combined organic layers were washed with brine (60 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (eluting with petroleum ether) to give the title compound.1H NMR (400 MHz, CDCl3): delta 7.58 (d, J = 2.2 Hz, 1H), 7.29 – 7.22 (m, 1H), 7.19 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-2-(trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 461432-23-5, 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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene (4.9 g, 15 mmol) and 20 mL of tetrahydrofuran were added to a 50 mL three-necked flask, and the mixture was stirred and cooled to -5 to 0 C.Isopropylmagnesium chloride Grignard reagent (8 mL, 2 mol/L) was slowly added dropwise, and the system was stirred at 0 C for 2 h.In another 100mL three-neck bottle, add(2R,3R,4S,5R,6R)-2-bromo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-tripivalyl ester (IIb, 5.8 g , 10 mmol), tetramethylethylenediamine (5 wt%),Cobalt triacetylacetonate (5 wt%) and 20 mL of tetrahydrofuran were cooled to 0 C.Slowly add the Grignard reagent in the previous 50mL bottle and add it in about 30min.The system was warmed to 25-30 C, stirred under heat for 2 h, and the system was quenched with 1N aqueous hydrochloric acid.The organic phase was extracted with EtOAc, brine and brine.Column chromatography (PE/EA = 6/1) gave the target product (5.4 g, yield 72%).

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-1-chloro-2-(4-ethoxybenzyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Fangnan Biological Technology Co., Ltd.; Zhang Nian; (6 pag.)CN104059041; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics