Tag: M.W=200-300

1996-29-8, 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, A new synthetic method of this compound is introduced below.

1-Bromo-4-chloro-2-fluorobenzene (5.68 g, 27.11 mmol) was dissolved in a reaction flask containing anhydrous tetrahydrofuran (60 mL) under nitrogen. The reaction solution was cooled to -78 C.LDA (11.44 mL, slowly added dropwise with stirring)2M tetrahydrofuran solution). After the addition is continued for 1 hour,Pass dry carbon dioxide gas and slowly raise to room temperature.After the reaction is complete, cool again to 0 C,It was quenched with saturated aqueous NaHCO3 (EtOAc) (EtOAc)Discard the organic phase. After the aqueous phase is adjusted to pH 2 to 3 with 3N hydrochloric acid,It was extracted with ethyl acetate (100 mL¡Á3) and the combined organic phases were washed with saturated brine.Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.3-Bromo-6-chloro-2-fluorobenzoic acid (3.4 g, yellow solid, yield 49.4%).

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; Beijing Yue Zhi Kangtai Bio-pharmaceutical Technology Co., Ltd.; Duan Maosheng; Xiong Yanlin; Liu Jiale; Tian Shihong; Dai Quan; (57 pag.)CN109232533; (2019); A;,
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2770-11-8, These common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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.

A solution of 2-(4-chloro-phenoxy)-phenylamine (100 mg, 0.46 mmol) and 7V-(2-formyl- phenyl)-acetamide (74 mg, 0.46 mmol) in anhydrous DCM (5ml) was stirred at r.t. and to this was added MgSO4 (550 mg, 4.6 mmol) and the resulting mixture stirred for a further18h at r.t. The mixture was then filtered and the solid was washed with DCM. The filtrate was then evaporated to dryness to yield the desired product. The product was identified by NMR, as no CHO peak was visible in the 1H NMR and it had been replaced with an imine peak. The product was used crude in all following experiments.

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 2770-11-8.

Reference:
Patent; STERIX LIMITED; WO2009/66072; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, 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 56961-77-4. 56961-77-4

1 15 g of 1 -Bromo-2,3-dichlorobenzene was dissolved in 470 g of toluene and the solution was cooled down to -10C. Then a 20% THF solution of isopropylmagnesium chloride (309 g) was added over 30 min and the reaction mixture was stirred 1 hour at -10C. Freshly distilled cyclopentadiene (44.5 g, 1 .3 eq) was added over 10 min. After one hour stirring at ambient temperature, the mixture was heated to reflux. When the conversion was completed, the reaction mixture was filtered off and washed twice with toluene. The mother liquor was evaporated and 106 g of brown crude oil was obtained (yield: 91 .5%. The material can be purified by distillation or by CC (silica gel, eluant: Hept TBME 19/1 ).1H-NMR (400 MHz, CDCI3): delta = 7.08-6.97 (m, 3H, Ar-H); 7.00-6.96 (m, 2H, Vinyl-H); 4.32- 4.31 (m, 1 H); 4.09-4.08 (m, 1 H); 2.46 (dt, J = 7.5 Hz, 1 .5 Hz, 1 H); 2.41 (dt, J = 7.0 Hz, 1 .5 Hz, 1 H).

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 1-Bromo-2,3-dichlorobenzene.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; DUMEUNIER, Raphael; SCHLETH, Florian; VETTIGER, Thomas; ROMMEL, Michael; TRAH, Stephan; WO2011/131545; (2011); A1;,
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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. 1996-29-8 name is 1-Bromo-4-chloro-2-fluorobenzene, 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. 1996-29-8

.1. Preparation of 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone A 3 L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95%, 84.6 g, 0.716 mol) and DMSO (400 mL, 4¡Á) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5¡Á). The resulting orange turbid solution was stirred for 15 min and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5¡Á). This mixture was then heated to 50 C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 min stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99%, solution yields of 3 and its regioisomer 4 were 83% and 17%, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737% water). THF (500 mL) was added, concentrated to 2¡Á solution (KF=0.158%). THF addition-concentration sequence was repeated to give a 2¡Á solution (KF=0.023%) which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; 1H NMR (400 MHz, CDCl3) delta 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); 13C NMR (100 MHz, CDCl3) delta 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; 1H NMR (400 MHz, CDCl3) delta 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); 13C NMR (100 MHz, CDCl3) delta 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-chloro-2-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Bednarz, Mark S.; Paul, Susan De; Kanamarlapudi, Ramanaiah C.; Perlberg, Anett; Zhang, Haiming; US2009/88447; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 51572-93-1, name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, molecular formula is C7H8Cl3NO, 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. 51572-93-1

General procedure: A mixture of substituted O-benzylhydroxylamine hydrochloride (1 equiv), TEA (1 equiv) and substituted salicylaldehyde (1 equiv) was dissolved in absolute ethanol and stirred for 0.5 h. The reaction was monitored by TLC. The precipitate was filtered and recrystallized from ethanol to gain salicylaldoxime (compounds 1g-20g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51572-93-1, its application will become more common.

Reference:
Article; Zhao, Ting-Ting; Lu, Xiang; Yang, Xian-Hui; Wang, Li-Ming; Li, Xi; Wang, Zhong-Chang; Gong, Hai-Bin; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 10; (2012); p. 3233 – 3241;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

19752-55-7, The chemical industry reduces the impact on the environment during synthesis 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, I believe this compound will play a more active role in future production and life.

Example S.3: Synthesis of 3,5-dichloro-2,2,2-trifluoro acetophenone (Compound example no.2 of table C.1 ); To 5.1 g (0.209 mol) Magnesium turnings was added 0.45 g of a 1 molar solution of DIBAL in hexane at 6O0C. After 15 min, 3,5-dichloro-bromobenzene (5.0 g, 0.022 mol) and 25 mL THF were added and the mixture was stirred. After start up of the reaction a mixture of 45g (0.2 mol) 3,5-dichloro-bromobenzene and 250 mL THF was added under reflux. After completion of the reaction the mixture was cooled to 00C and 31.1 g (0.219 mol) ethyl trifluoroacetate was added. After 2 h an aqueous solution of NH4CI was added an the mixture was separated between MTBE and aqueous NH4CI solution. The organic layer was separated and the solvent was removed in vacuum. (34.3g brown oil; purity 70percent ace. to g.c; yield 50percent)1H-NMR (360 MHz, CDCI3): delta = 7.7 (s, 1 H), 7.9 (s, 2H) ppm.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-dichlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BASF SE; Rack, Michael; Koerber, Karsten; WO2010/125130; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics