(4-bromo-2-(trifluoromethyl)phenyl)methanamine synthesis

Yield:1214372-39-0 77%

Reaction Conditions:

with dimethylsulfide borane complex in tetrahydrofuran at 0; for 1.5 h;Reflux;

Steps:

16.1

A solution of 18 ml of BH₃.Me₂S (180 mmol, 10M) was added slowly at 0° C. to a solution of 10.0 g (40.0 mmol) of 4-bromo-2-(trifluoromethyl)benzonitrile (Chem. Pharm. Bull. 2005, 53, 4, 402-409) in THF (110 ml). The mixture was stirred at 0° C. for 30 min, then warmed to 25° C. and stirred for 30 min. Subsequently, the mixture was heated under reflux for 30 min. After cooling to room temperature, the reaction mixture was admixed with 1M aqueous NaOH and extracted with ethyl acetate (3×150 ml). The combined organic phases were combined, dried over Na₂SO₄ and concentrated under reduced pressure. The resulting crude product was admixed at 0° C. with a solution of HCl in ethanol, and the mixture was stirred for 1 h. The mixture was concentrated under reduced pressure and the solid was washed with diethyl ether. 9.0 g (77%) of 1-[4-bromo-2-(trifluoromethyl)phenyl]methanamine hydrochloride were obtained.HPLC-MS: logP=0.92, mass (m/z): =254.09 (M+H)⁺.

References:

US2011/105532,2011,A1 Location in patent:Page/Page column 53