Benzyl Bromide → 3-(Benzyloxy)-4-nitrobenzaldehyde

Participants

Reaction Steps

In this synthesis the new (4-amino or substituted amino-3-hydroxyphenyl)-alkylnitriles of Formula (1), of this invention, where R2 is H, can be prepared by reaction of a 3-hydroxy-4-nitrobenzaldehyde of Formula (2) with a benzyl halide, such as benzyl bromide, in the presence of an inorganic base such as potassium carbonate in dimethylformamide (DMF) at room temperature for about 18 hours to produce the 3-benzyloxy-4-nitro-benzaldehyde compound of Formula (3) in about 98% yield; then reacting the compound of Formula (3) with diethyl cyanoalkylphosphonate of Formula (4) in a suspension of sodium hydride in anhydrous THF at room temperature for about 2 hours to produce 3-(3-benzyloxy-4-nitro-phenyl)-acrylonitrile of Formula (5) in about 100% yield; catalytically hydrogenating the compound of Formula (5) with 10% Pd on carbon at about 60 psi hydrogen at room temperature for about 4 hours to provide a compound of Formula (1) where R2 is H in about 100% yield.

Provenance & Evidence