2-Bromothiazole → 4-(1,3-Thiazol-2-yl)benzaldehyde

Participants

Reaction Steps

A mixture of NaHCO3 (3.83 g, 45.6 mmol) and 4-formylphenylboronic acid (2.69 g, 18.0 mmol) in water (60 mL) was added to a solution of 2-bromothiazole (2.50 g, 15.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (500 mg, 0.43 mmol) in DME (60 mL). The reaction mixture was heated to reflux for 18 h, cooled to room temperature, diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried with Na2SO4, and concentrated in vacuo. Two consecutive recrystallizations from hexanes/ethyl acetate yielded 998 mg (35%) of the title compound. MS 190 (M+H)+.

Provenance & Evidence