ChemicalBook CAS DataBase List 1-((4-Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid

1-((4-Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid synthesis

12synthesis methods

Product Name:1-((4-Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid
CAS Number:849217-48-7
Molecular formula:C11H10FNO3
Molecular Weight:223.2

Cyclopropyl-1,1-dicarboxylic acid(10 g, 77 mmol) in THF (100 mL) was cooled in an ice-water bath, and Triethylamine (8.0 g, 79 mmol) was added dropwise. The temperature of the ice bath during the dropping process is controlled below 10 degrees. The resulting solution was stirred for 30 minutes, and then thionyl chloride (SOCl2, 9.0 g, 76 mmol). Then, dropwise, 4-fluoroaniline (9.0 mL) of THF (30 mL) was added. The ice bath temperature during the whole dripping process is controlled below 10 degrees. The stirring continued for 4 hours, and the reaction was warmed to room temperature. The reaction was diluted with 200 mL of EtOAc And then washed with aqueous NaOH (1.0 M, 50 mL), water (40 mL), and saturated brine (40 mL). The resulting organic solution was dried over Na2SO4, suction filtered, and evaporated to ~ 30 mL. To the resulting viscous liquid was added heptane (200 mL), and a lot of flaky solid precipitated. Filtration and drying gave 1-((4-Fluorophenyl)carbamoyl) cyclopropane carboxylic acid (15.8 g, 93 percent).

372-19-0
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$10.00/1g

598-10-7 Synthesis

598-10-7
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$7.00/1g

1-((4-Fluorophenyl)carbamoyl)cyclopropanecarboxylic acid

849217-48-7
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$5.00/250mg

Yield:849217-48-7 75.5%

Reaction Conditions:

Stage #1:cyclopropane-1,1-dicarboxylic acid with thionyl chloride;triethylamine in dichloromethane for 0.5 h;Cooling with ice;
Stage #2:meta-fluoroaniline in dichloromethane at 20; for 1.5 h;Cooling with ice;

Steps:

1 Example 1. Preparation of 1- (4-fluorophenylcarbamoyl) cyclopropanecarboxylic acid
Compound 2-a (cyclopropane dicarboxylic acid, 0.13 g, 1.00 mmol) was dissolved in dichloromethane (10 ml)After stirring for 10 min in an ice bath, triethylamine (0.42 ml, 3.00 mmol) was added and thionyl chloride (0.143 g, 1.20 mmol) was added slowly to continue stirring atAfter stirring for half an hour under an ice bath, a solution of Compound 1-a (3-fluoroaniline, 0.123 g, 1.0 mmol) in methylene chloride(10ml), continue to stir in the ice bath for half an hour, return to room temperature and stir for 1h (TLC to monitor the reaction is complete). After the reaction is completed,The methylene chloride was recovered under reduced pressure, a saturated aqueous sodium chloride solution (40 ml) was added to the remaining reaction mixture, and the reaction liquid 3 was extracted with ethyl acetateThe combined organic phase was dried over anhydrous sodium sulfate and the solvent was recovered under reduced pressure. 0.21 g of a white solid (Intermediate 1) was obtained.Yield 75.5%;

References:

Hangzhou Xixi Hospital;Liu Shourong;Zhao Yanmei;Kong Limin;Zhou Hongping;Shao Yidan;Cai Zhaobin;Pan Xuwang;Xi Jianjun;Zhang Jiankang;Zhuang Rangxiao;Shi Tingting;Bao Jianfeng;Wang Weiwei;Liu Chuntao;Liu Fei CN106831707, 2017, A Location in patent:Paragraph 0059; 0060; 0061; 0062

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