Author: Jessica.F

These common heterocyclic compound, 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, 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. HPLC of Formula: C7H7BrClNO

A 500-mL round-bottom flask was charged with (E)-/er/-butyl 3-(3-methoxy-3-oxoprop-l-en-l-yl)-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate (Preparation 3a, (10.8 g, 26.0 mmol), xantphos (1.88 g, 3.25 mmol), cesium carbonate (25.4 g, 78.0 mmol), 4-bromo-5-chloro-2-methoxyaniline (6.15 g, 26.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.19 g, 1.30 mmol) and 1,4-dioxane (130 mL) then sparged with nitrogen for 15 min. The reaction mixture stirred vigorously for 20 h at ambient temperature. The reaction mixture was subsequently vacuum filtered through a 1.0 cm plug of silica gel and the pad was rinsed with EtOAc (3 x 150 mL). The filtrate was concentrated under reduced pressure to give a brown foam that was used immediately without further purification.[00562] The product was diluted with MeOH (260 mL) and transferred to a 350-mLpressure vessel equipped with a stir bar. The reaction vessel was subsequently charged with sodium methoxide (25 wt. % in MeOH, 2.97 ml, 13.00 mmol) and sealed with a Teflon cap equipped with a pressure-relief valve. The reaction vessel was placed in a 70 C oil bath and stirred vigorously. After 5 h, the reaction mixture was allowed to cool to ambient temperature, transferred to a 1-L round-bottom flask with additional MeOH and concentrated under reduced pressure. The brown oil was redissolved in DCM (150 mL) and filtered through a pad of Celite (3 cm) to facilitate loading the material onto a column. The Celite pad was rinsed with DCM (3 x 50 mL). The brown filtrate was concentrated under reduced pressure and purified by flash column chromatography (340-g Biotage column, eluent: gradient, 5 to 35% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford (Rac)-tert-butyl 1-(4-bromo-5-chloro-2-methoxyphenyl)-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate (9.12 g, 19.4 mmol, 74.7 % yield) as a tan solid.

The synthetic route of 4-Bromo-5-chloro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, 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 13918-92-8, Quality Control of 2,4-Difluorobenzene-1-sulfonyl chloride

To a cooled (0 C) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (13.7 g, 67.5 mmol) in pyridine (200 ml) was added slowly 2,4-difluorobenzenesulfonyl chloride (14.37 g, 67.6 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h. Most of the pyridine was removed in vacuo and the residue diluted with water (500 ml_). The solids were filtered off and washed with copious amounts of water to give 21 g of crude desired product. More solid appeared in the mother liquor and was filtered and washed with water to give an additional 1.5 g of desired material. The two batches were combined, triturated with 70 ml of methylene chloride, and dried in a vacuum oven at 50 0C to give the title compound (15 g)-LCMS (Method B) R1 = 1.11 min, MH+ = 378/380.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GLAXO GROUP LIMITED; HAMBLIN, Julie, Nicole; HARRISON, Zoe, Alicia; JONES, Paul, Spencer; KEELING, Suzanne, Elaine; LE, Joelle; LUNNISS, Christopher, James; PARR, Nigel, James; WO2010/102958; (2010); A1;,
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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 7006-52-2 as follows. HPLC of Formula: C7H8ClN

General procedure: N-Alkyl-substituted aniline (2 mmol) and Ru3(CO)12 in D2O(3mL) (Note: if toluene was needed, 1mL toluene was add as co-solvent) were stirred at 100-140°C in a sealed tube under a N2 atmosphere for 12 h. After the mixture was cooled to room temperature, water (10 ml) was added, and then extracted with diethyl ether (2×10 mL). The organic layer was washed with brine (5 mL), dried over anhydrous Na2SO4,and filtered. The filtrate was concentrated to afford the deuterated aniline product.

According to the analysis of related databases, 7006-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhan, Miao; Jiang, Hongxia; Pang, Xuehai; Zhang, Tao; Xu, Ruixue; Zhao, Lifeng; Liu, Yu; Gong, Yu; Chen, Yuanwei; Tetrahedron Letters; vol. 55; 36; (2014); p. 5070 – 5073;,
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Synthetic Route 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.

a 2-Chloro-4-fluorophenylisothiocyanate Into a solution of 2-chloro-4-fluoroaniline (500 mg, 3.44 mmol) in a mixture of chloroform and water (10 mL/10 mL) at room temperature, thiophosgene (0.53 mL, 6.88 mmol) and sodium bicarbonate (1.09 g, 10.32 mmol) were added. The mixture was stirred at room temperature for 16 hours. The mixture was partitioned between chloroform and water. The combined organic layer was then concentrated to give the desired product (586 mg, 91%). 1H NMR (CDCl3) delta 6.98 (m, 1H), 7.20 (m, 2H).

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

Reference:
Patent; Palovich, Michael R.; Widdowson, Katherine L.; Nie, Hong; US2003/216375; (2003); 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. 69957-83-1, name is N-Ethyl-4-chlorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H12ClN

[4-(2-{[2-(Methoxycarbonyl)phenyl]thio} ethyl) phenoxy] acetic acid (0.200 [G,] 0.577 mmol) was dissolved in DMF (10 ml), [N-(4-CHLOROBENZYL)-N-ETHYLAMINE] (0.108 g, 0.635 mmol) was added and the mixture was cooled to 0 C. N-[(1H-1, 2, 3-benzotriazol-1- yloxy) (dimethylamino) [METHYLENE]-N-METHYLMETHANAMINIUM] tetrafluoroborate (0.204 g, 0.635 mmol) and N-ethyl-N,N-diisopropylamine (0.157 g, 1.212 mmol) were added. The solution was stirred overnight at room temperature. Water (100 [ML)] was added and the water phase was extracted with diethyl ether (3 X 20ml). The organic phase was washed with [NA2CO3] (3 X 20 ml, [AQ)] and HCl (0.5 M, 2 X, 10 [ML).] The organic layer was dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromatography (started with isocratic heptane/EtOAc 30/70 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0. 063 [MM).] The product containing fractions were pooled and the solvent was removed by evaporation to give 0. [085 G OF METHYL 2-{ [2-(4-{2-[(4-CHLOROBENZYL)] (ethyl) [AMINO]-2-] oxoethoxy} phenyl) ethyl] thio} benzoate (yield 29.6%). [1HNMR] (rotamers, 300 MHz, CDC13) : 8 1.09-1. 21 [(M,] 3H), 2.91-2. 99 [(M,] 2H), 3.11-3. 18 [(M,] 2H), 3.32-3. 43 [(M,] 2H), 3.92 (s, [3H),] 4.57-4. 75 [(M,] 4H), 6.78, 6.92 (d, d, 2H), 7.12- 7.46 [(M,] 9H), 7.96 (d, [1H).]

According to the analysis of related databases, 69957-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/294; (2003); A1;,
Chloride – Wikipedia,
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Electric Literature of 14862-52-3, The chemical industry reduces the impact on the environment during synthesis 14862-52-3, name is 3,5-Dibromochlorobenzene, I believe this compound will play a more active role in future production and life.

3,5-dibromochlorobenzene (2.7 g, 10 mmol)9-phenylcarbazole-3-boronic acid (6.0 g, 21 mmol)Sodium carbonate (10.2 g, 96 mmol),Pd2 (dba) 3 (0.4 g, 0.4 mmol), toluene,Ethanol, water 50ml in turn added to the reaction bottle,The reaction was refluxed under nitrogen for 10 hours, cooled to room temperature,The aqueous layer was extracted with ethyl acetate,The organic layers were combined, washed with saturated brine and water, respectively,The organic layer was dried over magnesium sulfate, filtered,Filtrate spin dry, over silicone column,4.4 g of product was obtained, HPLC purity 99.2%.

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, 3,5-Dibromochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Yu Kaichao; Zhang Zhaochao; Wang Lichun; (35 pag.)CN107056806; (2017); A;,
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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. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-tert-Butyl-4-chlorobenzene

20 parts of water,40 parts of acetone,And 20 parts of potassium carbonate were mixed,Three parts of raw material A are added. After stirring for 1 hour,10 parts of raw material B was charged, the temperature was raised to 50 ° C. while stirring,Stir for an additional 1 hour. after that,Concentrate using a rotary evaporator,And dried to obtain a dispersant.N – (4 – aminophenyl) acetamide was used as the raw material A of the dispersant preparation example,Using 1-tert-butyl-4-chlorobenzene as the raw material B,Dispersant 1 was obtained.

According to the analysis of related databases, 3972-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dispersed materials Institute; Umemura, Kazuyuki; Ito, Shiho; Suzuki, Junji; Nishida, Atsushi; (15 pag.)JP2016/108519; (2016); A;,
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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 1005-56-7 as follows. Recommanded Product: 1005-56-7

Methyl-5-Jf-acetamido-3 , 5-dideoxy-3- f luoro- 8 , 9- 0-isopropylidene-4- O- (phenoxy) thiocarbonyl-D- eryt+/-ro-/?- L-manno-2 -nonulopyranosonate 19 :19To a solution of 18 (1.949 g, 5.1 mmol) in 70 mL dry DCM and 35 mL pyridine, phenylchlorothionoformate (761 muL, 5.6 mmol) was added at -400C and stirred for 30 minutes at this temperature. The mixture was then brought to room temperature and stirred for further 4 hours. MeOH (5 mL) was then added and after 10 minutes the -crude mixture was concentrated in .vacuo. and purified by column chromatography (EtOAc/MeOH 100:1) to give 19. Colorless solid (2.065 g, 76%) . 1H-NMR (400 MHz, CDCl3) delta 1.35 (s, 3H, Me2C), 1.40 (s, 3H, Me2C), 2.35 (s, 3H, NHAc), 3.49 (m, IH, H-5), 3.86 (s, 3H, OMe), 4.07 (dd, J = 21.5, 10.5 Hz, IH, H-9) , 4.37 (m, IH, H-9′), 4.45 (d, J = 4.9 Hz, IH, H-8), 4.58 (q, J = 2.7 Hz, IH, H-6), 5.16 (dd, J = 25.4, 1.7 Hz, IH, H-3), 5.69 (d, J = 3.6 Hz, IH, H-7), 6.11 (ddd, J = 8.7, 23.1 Hz, IH, H-4) , 6.25 (d, J = 8.2 Hz, IH, NHAc), 7.06 – 7.45 (m, 5H, OPh)

According to the analysis of related databases, 1005-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF BATH; WATTS, Andrew, Graham; WO2010/29302; (2010); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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 94-97-3, SDS of cas: 94-97-3

General procedure: A mixture of azole (0.2 mmol), ketone (0.3 mmol, 1.5equiv.), NaHCO3 (33.6 mg, 2.0 equiv.), I2 (101.6 mg, 2.0 equiv.), and 1,2-dichloroethane (2 mL) was stirred at 80 C for 24 h. After cooling to room temperature, the reaction mixture was quenched with a saturated solution of Na2S2O3 (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic phases were washed with brine (10 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatograph, using a mixture of petroleum ether and ethyl acetate (5:1-2:1) as eluent to afford the corresponding products. The identity and purity of the products was confirmed by 1H and 13C NMR spectroscopic analysis.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Chen, Wenlin; Yan, Rulong; Tang, Dong; Guo, Shuaibo; Meng, Xu; Chen, Baohua; Tetrahedron; vol. 68; 38; (2012); p. 7956 – 7959;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13918-92-8, 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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4.00 g (21.4 mmol) C-3, 4.3 mL (32 mmol) 2,4-difluorobenzenesulfonyl chloride, 5.2 mL (64 mmol) pyridine and 50 mL DCM is stirred at RT for 5 h. After completion of the reaction, the solvent is removed under reduced pressure, the crude product is taken up in 50 mL water and extracted twice with 100 mL DCM. The combined organic layers are dried over MgSO4 and the solvent is removed under reduced pressure. The crude product can be used without further purification. Yield: 7.88 g (91%).

The chemical industry reduces the impact on the environment during synthesis 2,4-Difluorobenzene-1-sulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; The designation of the inventor has not yet been filed; EP2546249; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics