Month: September 2021

Synthetic Route of 220227-21-4,Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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 19 1,1 -dimethylethyl (2S,4R)-2-methyl-4-{[(2,4,5-trifluorophenyl)sulfonyl]amino}-1- pyrrolidinecarboxylateTo 1 ,1-dimethylethyl (2S,4R)-4-amino-2-methyl-1-pyrrolidinecarboxylate (0.075 g, 0.38 mmol) in DCM (~5 mL) was added a solution of 2,4,5-trifluorobenzenesulfonyl chloride (0.075 g, 0.38 mmol) in DCM (~5 mL) and DIPEA (0.13 mL, 0.75 mmol). The resultant mixture was stirred at room temperature overnight, evaporated and loaded onto a 5 g silica SPE cartridge, eluting sequentially with DCM and ethyl acetate. The ethyl acetate fractions were combined and evaporated to afford the title compound (0.0942 g). LC-MS: m/z, 395 (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 2,4,5-Trifluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/26197; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 87851-77-2, The chemical industry reduces the impact on the environment during synthesis 87851-77-2, name is O-(3-Chloroallyl)hydroxylamine, I believe this compound will play a more active role in future production and life.

d) 2-(1-((E)-3-Chloro-2-propenyloxyimino)propyl)-5-(3,7-dioxabicyclo[4.1.0]hept-6-yl)-3-hydroxycyclohex-2-enone 7.9 g (29.5 mmol) of 2-(1-oxopropyl)-5-(3,7-dioxabicyclo[4.1.0]-hept-6-yl)-3-hydroxycyclohex-2-enone in 20 ml of methanol were mixed at room temperature with 3.5 g (32.4 mmol) of O-((E)-3-chloro-2-propenyl)hydroxylamine, and the mixture was stirred for about 10 hours. Concentration under reduced pressure gave an oil in quantitative yield which could be purified by chromatography over silica gel using cyclohexane/ethyl acetate. Yield 6.6 g. 1 H NMR (CDCl3): delta=1.13 (t); 1.93 (m); 2.20-2.75 (m); 2.90 (m); 3.13 (m); 3.50 (m); 3.98 (m); 4.52 (d); 6.10 (m); 6.35 (d); 14.3 (s).

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, O-(3-Chloroallyl)hydroxylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF Aktiengesellschaft; US6107254; (2000); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 883499-24-9, name is 1-Bromo-2-chloro-3-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 883499-24-9, SDS of cas: 883499-24-9

Under nitrogen environment,And at reflux temperature, 7-(diphenylamino)-9,9′-dimethyl-9H-fluoren-3-ol (100 g),1-bromo-2-chloro-3-fluorobenzene (58.3 g),The flask of potassium carbonate (91.5 g) and NMP (500 ml) was heated and stirred for 4 hours.After the reaction stopped, the reaction solution was cooled to room temperature, and water was added,The precipitate deposited was extracted by suction filtration. Use water in turn,After washing the obtained precipitate with methanol,Refined with silicone tubing (dissolved solution: toluene),Thus, 6-(3-bromo-2-chlorophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (150 g) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-chloro-3-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; KWANSEI GAKUIN EDUCATIONAL FOUNDATION; JNC CORPORATION; HATAKEYAMA, TAKUJI; MASUDA, KATSUYA; YAMAGA, YUKO; YANAI, MOTOKI; (214 pag.)TW2019/4977; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 54788-38-4, These common heterocyclic compound, 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, 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.

Referecne Example 1; (3-Bromophenyl) (4-chloro-2-hydroxy-5-methylphenyl) methanone; Aluminum chloride (20.4 g) was added to a solution of 3-chloro-4-methylanisole (20 g) in chlorobenzene (56 ml) at 20-30C, and then 3-bromobenzoyl chloride (28 g) was further added dropwise over about 30 minutes at 25 to 30C. After completion of addition, the mixture was stirred at 25C for 1 hour, and then heated at 40C for 1 hour. After the reaction was completed, the mixture was cooled, and toluene/tetrahydrofuran (1: 1,200 ml) was added dropwise at 20 to 30C. Then, 4N hydrochloric acid (80 ml) was added dropwise. The organic layer was separated, washed successively with 2N hydrochloric acid (60 ml) and a 10% aqueous sodium chloride solution. The organic layer was concentrated to 80 g. After methanol (100 ml) was added, the mixture was concentrated again to 90 g. Methanol (80 ml) was added to the residue, the mixture was stirred at room temperature for 30 minutes, and below 5C for 1 hour. Crysatls were collected, washed with cooled methanol (40 ml) and dried under reduced pressure to obtain the title compound (35.4 g, yield 85.1 %). H-NMR (300MHz, CDC13) 5 (ppm): 2.28 (3H, s), 7.12 (1H, s), 7.36-7. 42 (2H, m), 7.54-7. 57 (1H, m), 7.72-7. 80 (2H, m), 11.7 (1H, s).

The synthetic route of 54788-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/82879; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 623-12-1, name is 1-Chloro-4-methoxybenzene, 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. Recommanded Product: 1-Chloro-4-methoxybenzene

General procedure: A Schlenk flask was charged with aryl chlorides (0.20 mmol), arylboronic acids (0.30 mmol), N-heterocyclic carbenepalladium(II) complex 3 (2 mol %), KOtBu (2.0 equiv), iPrOH(1 mL) and H2O (1 mL). The mixture was stirred at 80 C for 15 h under N2. After cooling, the reaction mixture was evaporated andthe product was isolated by preparative TLC on silica gel plates. The purified products were identified by 1H NMR spectra and their analytical data are given in Supporting Information.

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

Reference:
Article; Wang, Tao; Xie, Huanping; Liu, Lantao; Zhao, Wen-Xian; Journal of Organometallic Chemistry; vol. 804; (2016); p. 73 – 79;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, 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. Computed Properties of C6H3BrClF

Step 1 Ethyl 2′-chloro-4′-fluorobiphenyl-2-carboxylate To a reaction vessel were added 1-bromo-2-chloro-4-fluorobenzene (25 g), ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (46 g), toluene (125 ml), water (125 ml) and tripotassium phosphate (50.5 g), and the reaction vessel was substituted with argon. To this mixture was added dichlorobis(triphenylphosphine)palladium(II) (1.67 g) and the mixture was stirred at an oil bath temperature 110 C. for 3 hr. The reaction vessel was removed from the oil bath, and water (125 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 hr and filtered through celite. The filtrate was partitioned by pouring into a separating funnel. The aqueous layer was extracted with toluene, and combined with the organic layer. The organic layer was washed twice with water (125 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (41.8 g). The obtained solid was used for the next reaction without further purification. 1H-NMR (400 MHz, CDCl3) delta: 8.06-8.02 (1H, m), 7.60-7.54 (1H, m), 7.52-7.45 (1H, m), 7.27-7.16 (3H, m), 7.06-7.00 (1H, m), 4.18-4.09 (2H, m), 1.11-1.06 (3H, m).

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

Reference:
Patent; JAPAN TOBACCO INC.; Motomura, Takahisa; US2014/296316; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3,6-Dichloro-1,2,4,5-tetrazine

To a solution of 3,6-dichloro-1,2,4,5-tetrazine (1.51 g, 10 mmol) in acetonitrile (70 ml) was added the sodium salt of 5-amino-1H-tetrazole (2.14 g, 10 mmol). The mixture was refluxed for 24 hours then allowed to cool to room temperature. The suspension was centrifuged until the supernatant liquid was clear. The liquid was decanted and the brown solid washed successively with acetonitrile and water. With each wash the solid was separated from the solvent by centrifugation followed by decantation. The isolated crude yield was 1.5 g (60%), this material was recrystallized from DMSO/methanol yielding an orange brown powder mp 264 C. dec; 1H NMR(deuteriomethylsulfoxide) 12.5(b,r s,4H); 13 C NMR (deuteriomethylsulfoxide) 151.74, 158.25; IR (KBr) 3421, 3000, 1615, 1436, 1127 cm-1. A gas pycnometer density of 1.76 g/cm3 was also determined and a drop height of 195 cm was measured (Type 12, HMX=24-27 cm).

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 106131-61-7.

Reference:
Patent; The Regents of the University of California; US6657059; (2003); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4261-67-0, 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. 4261-67-0 name is 3-Chloro-N,N,2-trimethylpropan-1-amine hydrochloride, 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.

EXAMPLE 3 Cis(+)-3-acetyloxy-2,3-dihydro-5-(2-methyl-3-dimethylaminopropyl)-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one oxalate (diastereoisomer B) 5 g cis(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one, 2.9 g 2-methyl-3-dimethylaminopropylchloride hydrochloride, 5.7 g K2 CO3, 1.4 ml H2 O were reacted in 75 ml acetone, according to the procedure as in Example 1 (a), then reacted with 70 ml acetic anhydride, (see Example 1 (b)). The crude was treated with ethyl ether and the so obtained solid is filtered off and the solution was evaporated to dryness. This procedure was repeated. 4.3 g residue were dissolved in isopropyl alcohol and treated with 1.2 g oxalic acid. A solid, which was crystallized from acetone-ethyl ether, was obtained; m.p. 84°-89° C.; [alpha]D20 =119.3 (H2 O).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-N,N,2-trimethylpropan-1-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Istituto Luso Farmaco d’Italia S.p.A.; US5571807; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 69411-05-8, 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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

The synthetic route of 3-Chloro-5-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrClF

To a stirred solution of l-Bromo-4-chloro-2-fluorobenzene Al (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 1 % NaCl solution (2.0 L). The organic layer was dried over anhydrous Na2SC , 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): delta 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).

The synthetic route of 1996-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BABU, Suresh; BELEMA, Makonen; BENDER, John A; IWUAGWU, Christiana; KADOW, John F.; KUMARAVEL, Selvakumar; NAGALAKSHMI, Pulicharla; NAIDU, B. Narasimhulu; PATEL, Manoj; PEESE, Kevin M; RAJAMANI, Ramkumar; SAULNIER, Mark; WANG, Alan Xiangdong; (536 pag.)WO2018/203235; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics