Potassium Carbonate → 3-Phenylfuran-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Prepare a mixture of 3-bromofuran-2-carbaldehyde (381 mg, 2.19 mmol), phenylboronic acid (534 mg, 4.38 mmol), and 2M potassium carbonate (3.28 mL, 6.57 mmol) in 1,2-dimethoxyethane (20 mL). Bubble nitrogen into this mixture for 20 minutes. Add Pd2(dba)3 (68 mg, 0.06 mmol) and PPh3 (68 mg, 0.26 mmol) and purge the mixture with nitrogen for an additional 10 minutes. Then heat the mixture to 80° C. After 24 hours, evaporate the solvent and redissolve the residue in ethyl acetate. Extract the aqueous phase with ethyl acetate (2×10 mL), wash the combined organic phases with brine (40 mL), dry (magnesium sulfate), filter and concentrate. Perform flash chromatography on silica gel eluting with 5:1 hex/ethyl acetate to afford 405 mg of the title compound as a white solid. MS: m/e=173 [MH+]

Provenance & Evidence