Water → 3'-Methylaminobiphenyl-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

5 g (26.8 mmol) of 3-bromophenylmethylamine and 4 g (26.8 mmol) of commercial 4-formylbenzeneboronic acid are dissolved in 50 mL of an aqueous 6/1 mixture of dimethylformamide/aqueous 2 M potassium phosphate. 1.5 g (1.3 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium are added. The mixture is stirred for 2 hours at 90° C. The reaction is worked up by addition of 50 mL of water and extraction with ethyl acetate. The organic phases are washed with sodium chloride solution and dried over magnesium sulfate. The solvents are evaporated off, and the residue is then purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 4.3 g (76%) of 3′-methylaminobiphenyl-4-carbaldehyde are obtained.

Provenance & Evidence