4-Fluorobiphenyl → 1-Chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

Participants

Reaction Steps

A solution of 26.25 g of 1-chloro-3-(4'-fluoro-4-biphenylyl)-butane [obtainable by a Friedel-Crafts reaction of 4-fluoro-biphenyl with 3-chloropropionyl chloride to give 4'-fluoro-4-(3-chloropropionyl)-biphenyl (m.p. 96° - 97° ), reaction with CH3MgI to give 1-chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol (m.p. 78° - 79° ) and reduction using HI] in 150 ml of absolute ethanol is added dropwise at 0° to a solution of 10 g of NH3 in 150 ml of absolute ethanol. The solution is stirred for a further 2 hours at 20°, concentrated and worked up with aqueous sodium hydroxide solution and ether to give 3-(4'-fluoro-4-biphenylyl)-butylamine; hydrochloride, m.p. 222° - 224°.

Provenance & Evidence