Category: 168268-00-6

Adding a certain compound to certain chemical reactions, such as: 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, belongs to ethers-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 168268-00-6, name: 4-(Benzyloxy)-3-fluoroaniline

A solution of 1.23 L of acetone and 600 ml of water in sodium carbonate (132 g, 1.25 mol) was added to the oil and thenCool down to 05C, add benzyl chloroformate (127.8g, 0.748mol) dropwise, continue stirring for 15min,Filtration gave 133 g of a yellow solid as a compound of formula (4) with a yield of 98.9%.

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Reference:
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Zeng Huang; Zhang Zixue; Liu Yu; Pan Deng; Zou Lei; Zhang Yi; (8 pag.)CN108069919; (2018); A;,
Ether – Wikipedia,
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Application of 168268-00-6,Some common heterocyclic compound, 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, molecular formula is C13H12FNO, 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 mixture of 4-benzyloxy-3-fluoroaniline (6.06 g, 27.9 mmol) (U.S. Pat. No. 5,622,967) and ethyl (ethoxymethylene)cyanoacetate (5.08 g, 30.0 mmol) is heated at 120 C. for 45 minutes then cooled to room temperature. This solid is added in portions to a 3:1 mixture of diphenyl ether:biphenyl at 245 C. This mixture is heated at 245 C. for 3 hours then cooled and the solids are collected by filtration, washing with hexane and diethyl ether to provides 2.60 g of 6-benzyloxy-7-fluoro-4-oxo-1, 4-dihydro-3-quinolinecarbonitrile, mp>250 C. [0198] MS 293.1 (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-(Benzyloxy)-3-fluoroaniline, its application will become more common.

Reference:
Patent; Wyeth Holdings Corporation; US2003/212276; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, A new synthetic method of this compound is introduced below., name: 4-(Benzyloxy)-3-fluoroaniline

4-Benzyloxy-3-fluoro-aniline (55 g), isopropyl alcohol (550 ml) and (R)-glycidyl butyrate (36.6 g) were taken into a reaction flask at room temperature (25-30C), and the resulting mass was heated to reflux and then stirred for 28 hours at the same temperature. After completion of the reaction, the solvent was distilled under vacuum to obtain a residue. Diisopropyl ether (560 ml) was added to the residue at the room temperature and theresulting solution was heated to reflux, followed by stirring for 15 minutes at the same temperature. The reaction mass was cooled to 25-30C and then stirred for 30 minutes at the same temperature. The separated solid was filtered and then washed with diisopropyl ether (100 ml) to produce 62 g of (2R)-3-(4-benzyloxy-3-fluoro-phenylamino)-2-hydroxy- propyl butanoate (Purity by HPLC: 98.6%).

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; SYMED LABS LIMITED; MOHAN RAO DODDA; MALLA REDDY VANGA; JITHENDER AADEPU; (95 pag.)WO2016/79757; (2016); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 168268-00-6, A common heterocyclic compound, 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, molecular formula is C13H12FNO, 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.

To a stirred mixture of 4-benzyloxy-3-fluoro-phenylamine (155.3 mmol, 33.7 g), 1- (4-FLUORO-PHENYLCARBAMOYL)-CYCLOPROPANECARBOXYLIC acid (170.8 mmol, 38.13 g) and anhydrous dichloromethane (600 ml) was added EDCI (233.9 mmol, 44.7 g) in portions. After stirring at RT for 1 hr, the reaction mixture was diluted with saturated sodium bicarbonate (400 ml) and stirred for 30 minutes. The precipitate was filtered and air dried to give the 1ST CROP of product. The biphasic filtrate was separated, and the organic phase was washed with brine (300 ml), dried over sodium sulfate, and concentrated. The residue was taken up in DCM (100 ml), stirred for 15 minutes, and filtered to give a 2ND crop of product. The combined yield of cyclopropane-1, 1- dicarboxylic acid (4-benzyloxy-3-fluoro-phenyl) -amide (4-fluoro-phenyl) -amide was 64.5 g (98%).

The synthetic route of 168268-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; WO2005/30140; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 168268-00-6, 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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 4-(benzyloxy)-3-fluoroaniline (1.04 g, 4.8 mmol) (WO 2005030140) under a nitrogen atmosphere was added acetic acid (2.3 ml_, 38.3 mmol), triethy lorthoformate (2.44 ml_, 14.4 mmol) and sodium azide (0.34 g, 5.3 mmol), and the reaction mixture heated at 95 C for 2.5 hours. The solution was then allowed to cool to room temperature, and water was added followed by extraction with ethyl acetate three times. The extracts were combined and washed with brine and dried over magnesium sulfate. The mixture was filtered and concentrated under reduced pressure, and the crude material purified by chromatography on silicon gel (20 – 40 % ethyl acetate in heptane) to give the title compound as a white solid (1.12 g, 86 %). 1H NMR (400 MHz, deuteromethanol) delta 9.65 (s, 1 H), 7.73 – 7.68 (dd, 1 H, J=1 1 , 2.5 Hz), 7.60 – 7.57 (m, 1 H) 7.47 – 7.45 (m, 2H), 7.40 – 7.30 (m, 5H), 5.24 (s, 2H); LCMS (ES+): 271 .1 (M+1 ).

The chemical industry reduces the impact on the environment during synthesis 4-(Benzyloxy)-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.; WO2012/69948; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H12FNO

To a stirred mixture of 4-benzyloxy-3-fluoro-phenylamine (33.7 g, 155.3mmol), 1-(4-fluoro-phenylcarbamoyl)-cyclopropane carboxylic acid (38.13 g, 170.8mmol) and anhydrous DCM (600 ml) was added EDCI (44.7 g, 233.9mmol) in portions. After stirring at r.t. for 1 h, the reaction mixture was diluted with saturated sodium bicarbonate (400 ml) and stirred for 30 minutes. The precipitate was filtered and air dried to give the 1st crop of product. The biphasic filtrate was separated, and the organic phase was washed with brine (300 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was taken up in DCM (100 ml), stirred for 15 minutes, and filtered to give a 2nd crop of product. The combined yield of Cyclopropane-1,1-dicarboxylic acid (4-benzyloxy-3-fluoro-phenyl)-amide(4-fluoro-phenyl)-amide 64.5 g, yield: 98%. 1H-NMR (300MHz, CDCl3) delta: 8.9 (m, 2H), 7.35-7.18 (m, 8H), 6.95-6.85 (m, 4H), 5.03 (s,2H), 1.53(s, 2H).

According to the analysis of related databases, 168268-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jieming; Gu, Weijie; Bi, Xinzhou; Li, Huilan; Liao, Chen; Liu, Chunxia; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6674 – 6679;,
Ether – Wikipedia,
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