Potassium Carbonate → 6-Nitrobiphenyl-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A 250-mL 3-necked round-bottom flask was placed a solution of 2-chloro-3-nitrobenzaldehyde (5.3 g, 28.57 mmol, 1.00 equiv) in toluene (50 mL), phenylboronic acid (3.83 g, 31.39 mmol, 1.10 equiv), K2CO3 (7.88 g, 57.10 mmol, 2.00 equiv) in water (30 mL) and Pd(PPh3)4 (660 mg, 0.57 mmol, 0.02 equiv). The resulting mixture was heated to 110° C. for 30 hours. Upon completion, the reaction mixture was cooled and diluted with Et2O (1000 mL). After phase separation, organic layers were dried over anhydrous magnesium sulfate, filtered off and concentrated on rotary evaporator. The residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:50) affording 6-nitrobiphenyl-2-carbaldehyde as yellow solid (5.35 g, 82%).

Provenance & Evidence