Category: chlorides-buliding-blocks

These common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, 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: 2-Chloro-4-fluoroanisole

To concentrated sulfuric acid (100mL) solution of2-chloro-4-fluoro anisole (38g, 237mmol), bromine (19mL, 737mmol) was addedunder ice-cooling, and the mixture was stirred for 1.5 hours. the reactionsolution was added gradually into ice water and extracted with diethyl ether(300mL × 3). After washing the organic layer with 5% aqueous sodium thiosulfatesolution (300 mL), the organic layer was dried over anhydrous magnesiumsulfate, filtered, and the crude product obtained through concentration underreduced pressure was purified by silica gel chromatography (hexane: ethylacetate = 1 : 0~10: 1) to give white solid of 5-bromo-2-chloro-4-fluoro anisole(8.0 g, yield: 14%) and white solid of 2-bromo-6-chloro-4- fluoro anisole (16.7g, yield: 30%).

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

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; MATSUKAWA, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (75 pag.)JP2016/56157; (2016); A;,
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Synthetic Route of 20850-43-5,Some common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, molecular formula is C8H7ClO2, 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.

Under argon atmosphere, 17.5 ml of 1.58M n-butyl lithium-n-hexane solution was dropped into a mixture of 25 ml of tetrahydrofuran and 2.78 g of diisopropylamine under cooling ice, followed by 30 minutes’ stirring under the same condition. Thereafter a solution of 2.50 g of 1-tert-butoxycarbonyl-3-oxopiperazine (which was prepared by following Tetrahedron Lett., 1980, 21, 3019 – 3020) in 60 ml of tetrahydrofuran was added by dropping under cooling with ice, followed by 3 hours’ stirring under the same condition, further dropping of a solution of 2.30 g of 5-chloromethyl-benzo[1,3]dioxole in 20 ml of tetrahydrofuran under cooling with ice, and an hour’s stirring under the same condition. The solution was warmed to room temperature and stirred for 18 hours. After addition of saturated aqueous ammonium chloride solution, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and the solvent was distilled therefrom under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate) to provide 2.84 g (68%) of 2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonyl-3-oxopiperazine. 1H-NMR(CDCl3)delta:6.67(s,1H),6.65(d,J=1.3Hz,2H),5.90(s,2H), 4.52~4.43(m,1H),4.12(d,J=7.2Hz,2H),3.23(t,J=5.1Hz,2H), 2.57(t,J=5.8Hz,2H),1.45(s,9H) Mass,m/e:334(M+),278,144,57(base)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Chloromethyl)benzo[d][1,3]dioxole, its application will become more common.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP1724267; (2006); A1;,
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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. 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H6Cl2

General procedure: In the initial mixed solution prepared in the round flask in Example 1, 3-chloro-2-(chloromethyl)prop-1-ene(50 [mu] L, 0.47 mmol)By following the same procedure as in Example 1 except for using 1-pyrene methanol (240 mg, 1.03 mmol)Experiments were conducted to obtain a solid state of the compound containing pyrene dimer, 120 mg in 49% yieldOctane-1,8-diol (99 mg, 0.68 mmol) (1 eq.)And 1-(bromomethyl)pyrene (440 mg, 1.49 mmol) (2.2 eq.),3 mL ([diol] = 50 mM) in anhydrous dimethylformamide in (DMF)To room temperature in the presence and condition of N2 and NaH (3 eq.), It was added to the round bottom flask. The mixed solution in the flask was stirred at room temperature for 1 hour.After that,Then quenched and diluted with distilled water was added to the solution.next, The organics were extracted by the addition of methyl-dichloro (DCM) to the mixed solution,The resulting organic layer was again distilled under reduced pressure to reotgo so that solution filtered through a filter containing sodium sulfate (Na2SO4).The resultant was purified by silica gel column chromatography (EtOAc: Hexane = 1: 5 (volume ratio)) of the solid state compound containing pyrene dimer increasing the purity of the resultant using,To give the 120 mg at a yield of 31%.

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 1871-57-4.

Reference:
Patent; Inha UniversityIndustry-AcademicCooperation Foundation; Jo, Dong Gyu; (29 pag.)KR101542140; (2015); B1;,
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Reference of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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 the stirred suspension of p-methoxybenzyl alcohol (2.00 g, 14.5 mmol)and N-phenyl-2,2,2-trifluoroacetimidate chloride (3.40 g, 16.3 mmol) inDCM (70 mL), NaH (60% in mineral oil, 0.635 g, 15.8 mmol) was added portionwise at 0C.The mixture was stirred for 2h at rt. After an addition of ice, the organic phase was washedwith water (3 x 40 mL), dried (MgSO4), filtered, and evaporated. The resulting residue wascrystallized from Et2O/PE, to give 1 as white needles (4.00 g, 89%). mp 90-91C, 1H NMR(360 MHz in CDCl3, ppm): delta 7.37 (2H, br d, J = 8.5 Hz, Ph), 7.29 (2H, br t, J = 2.0 Hz, J =6.5 Hz, J = 7.5 Hz, Ph), 7.08 (1H, br t, J = 1.0 Hz, J = 7.0 Hz, J = 7.5 Hz, Ph), 6.92 (2H, br d,J = 8.5 Hz, Ph-OCH3, PMB), 6.82 (2H, br d, J = 8.5 Hz, Ph-OCH3, PMB), 5.25 (2H, s, CH2,PMB), 3.83 (3H, s, OCH3, PMB), 13C NMR (90 MHz in CDCl3, ppm): delta 160.08 (Cquat-OCH3,PMB), 145.28 (q, JC-C-F = 35,0 Hz), 144.58 (Cquat arom), 130.42, 128.89, 127.23, 124.04,119.73 (CH arom), 116.38 (q, JC-F = 285,5 Hz), 114.13 (Cm PMB), 69.69 (CH2,PMB), 53.32 (OCH3, PMB), HRMS (ESI) m/z [M+Na] 332.0869; found 332.0859, AnalCalcd C16H14F3NO2 : Calcd. C 62.13, H 4.56, N 4.53; found C 62.30, H 4.59, N 4.44.

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

Reference:
Article; Barroca-Aubry, Nadine; Benchekroun, Mohamed; Gomes, Filipe; Bonnaffe, David; Tetrahedron Letters; vol. 54; 37; (2013); p. 5118 – 5121;,
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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. 4152-90-3, name is (3-Chlorophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4152-90-3

Compound (E) (12.5 g, 45.9 mmol) prepared in the step 4 was dissolved in tetrahydrofuran (400 mL), then triethylamine (19.2 ml, 3 equivalents) and 3-chlorobenzylamine (11.2 mL, 2 equivalents) were added and the mixture was stirred at 40°C for 20 hours. The salt separated out therefrom was removed by filtration and the solvent was evaporated. The residue was purified by a chromatography (chloroform:methanol = 100:1 –> 40:1) and a mixed solvent of hexane/ethyl acetate (3:1) was added to a concentrated residue of a fraction containing the objective substance so that the crystals were separated out. The suspension containing the crystals was stirred for 1 hour and the crystals separated out therefrom were filtered and dried in vacuo to prepare compound (F) (11.9 g, yield: 69percent).

According to the analysis of related databases, 4152-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1547616; (2005); A1;,
Chloride – Wikipedia,
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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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-4-chloro-2-fluorobenzene

Carbazole (20.0 g, 119.6 mmol) and KF-alumina (30.0 g, 179.4 mmol) under a stream of nitrogenAnd 18-crown-6 (6.3 g) was placed in 120 mL of dimethyl sulfoxide (DMSO; Dimethylsulfoxide) solvent and stirred with heating.1-Bromo-4-chloro-2-fluorobenzene (25.1 g, 119.6 mmol) was added under reflux.After stirring for 8 hours, it was cooled to normal temperature, and the resulting solid was filtered to obtain a compound of the formula 2-2-A (35.1 g, yield 83%).

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 1996-29-8.

Reference:
Patent; Co., Ltd. LG Chemical; Han Meilian; Li Dongxun; Xu Jingwu; Zhang Fenzai; Xu Dongxu; Zheng Minyou; (51 pag.)CN108218802; (2018); A;,
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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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., COA of Formula: C6H3ClF2O2S

General procedure: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

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:
Article; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
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Application of 27139-97-5, 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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(b) 50 g of compound 3, 50 g of NBS (ie N-bromosuccinimide), 0.3 g of BPO (ie dibenzoyl peroxide) and 300 mL of carbon tetrachloride were added to a 500 mL three-necked flask, and the external temperature was raised to At 90 C, the reaction was carried out for 24 h (at this time, TLC showed complete reaction);Pour the reaction solution into 500 mL of ice water, adjust the pH to 10 with 2N (equivalent concentration) sodium hydroxide solution, extract the layers, combine the organic phases, and wash with 5% sodium bicarbonate (mass concentration, the same below) solution. After drying, it was spin-dried, and column chromatography was carried out to obtain 52 g of Compound 4 (yield: 75%) (the nuclear magnetic spectrum of Compound 4 is shown in Fig. 3, and the specific resolution is: 1H NMR (400 MHz, CDCl3) delta (ppm): 7.58 ( d, J = 2.0 Hz, 1H), 7.38 (d, J = 4.0 Hz, 1H), 7.28 (d, J = 4.0 Hz, 1H), 4.55 (s, 1H))

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, 2-Bromo-4-chloro-1-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Liu Ke; (11 pag.)CN108707112; (2018); A;,
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Reference of 6579-54-0, 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 6579-54-0 as follows.

General procedure: To a stirred solution of 4 (1.0 mmol) in THF (5 mL) was added appropriate sulfonyl chloride (1.1 mmol) and NaHCO3 (38 mmol). The reaction mixture was stirred at room temperature for 4 h under nitrogen atmosphere. Then the solvent was evaporated in vacuum. The residue was diluted with water. The whole mixture was extracted with AcOEt for three times. The combined organic layer was washed with water, sat. brine, and dried over Na2SO4. The crude product was purified by column chromatography using petroleum ether/AcOEt (10/1-8/1, v/v) as eluent to afford F01-F35.

According to the analysis of related databases, 6579-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wen-Ming; Yao, Yang; Yang, Teng; Wang, Xue-Ying; Zhu, Zhen-Yun; Xu, Wen-Tao; Lin, Hai-Xia; Gao, Zhao-Bing; Zhou, Hu; Yang, Cai-Guang; Cui, Yong-Mei; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1943 – 1948;,
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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. 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2,3-dichlorobenzene

Intermediate 45:[0178] To a -30C solution of l-bromo-2,3-dichlorobenzene (10 g, 44 mmol) in THF (120 mL) was added z-PrMgCl (2.0 M in THF, 35 mL, 70 mmol) at a rate such that the temperature < -20C. Meanwhile, to a -10C solution of Cul (420 mg, 2.2 mmol) in THF (120 mL) was added pyridine (7.1 mL, 88 mmol) and then benzyl carbonochloridate (9.7 mL, 68 mmol) such that the temperature < 0C. To this heterogeneous mixture was added the initially formed Grignard at a rate such that the temperature < 0C. The resulting solution was stirred at 0C for 30 min and then allowed to warm to rt. The reaction was then quenched with 10% aq NH4C1. EtOAc was added and the blue aq layer was removed. The organic layer was washed with 10% aq H4CI, 1 N HC1, and a 20% aq NaCl solution. The organic layer was then concentrated and the residue was dissolved and crystallized from MeOH. The slurry was filtered and the filtercake washed with MeOH to give benzyl 4-(2,3-dichlorophenyl)pyridine-l(4H)- carboxylate (intermediate 45) (12 g, 76%) as an off-white solid. HPLC: 99%, RT 4.118 min. MS (ESI) m/z 382.0 [M + Na]+. mp: 69-70C. 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; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; JIN, Jian; ROTH, Bryan; FRYE, Stephen; WO2012/3418; (2012); A2;,
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