ChemicalBook CAS DataBase List 4-(BROMOMETHYL)-2-FLUOROBENZONITRILE

4-(BROMOMETHYL)-2-FLUOROBENZONITRILE synthesis

14synthesis methods

Product Name:4-(BROMOMETHYL)-2-FLUOROBENZONITRILE
CAS Number:222978-03-2
Molecular formula:C8H5BrFN
Molecular Weight:214.03

85070-67-3

222978-03-2

2-Fluoro-4-methylbenzonitrile (10 g, 74.07 mmol) was used as a raw material, which was dissolved in 200 mL of chloroform, 1 g of benzoyl peroxide (BPO) was added, and stirred until completely dissolved. Subsequently, N-bromosuccinimide (NBS, 19.77 g, 11.11 mmol) was added in batches and the reaction mixture was refluxed for 12 hours. After completion of the reaction, it was cooled to room temperature and washed three times with saturated aqueous sodium bicarbonate solution, then three times with appropriate amount of water and finally three times with saturated brine. The solvent was removed by evaporation under reduced pressure and purified by column chromatography to give the light yellow liquid product 4-cyano-3-fluorobenzyl bromide (14.00 g) in 88.79% yield.

85070-67-3 Synthesis

85070-67-3
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222978-03-2
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Yield: 88.79%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in chloroform for 12 h;Reflux;

Steps:

1 4-nitrile-3-fluorobenzyl chloride (2)Of the preparation11
3-fluoro-4-nitrile toluene 1 (10 g, 74.07 mmol)Dissolved in chloroform 200mL,Add BPO 1g, stirring dissolved,NBS (19.77 g, 11.11 mmol) was added portionwise,Reflux 12h,Cooling, the reaction solution with saturated aqueous solution of sodium bicarbonate 3 times wash,Wash the amount of water 3 times, the amount of saturated salt water washed 3 times, evaporation of the solvent under reduced pressure, column chromatography was pale yellow liquid 14.00g, yield88.79%.

References:

China Pharmaceutical University;Li Zhiyu;Bian Jinlei;Xu Xi;Ge Raoling CN106810552, 2017, A Location in patent:Paragraph 0068; 0070; 0071

452-74-4 Synthesis