Potassium Carbonate → 4'-Chlorobiphenyl-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

2-Bromobenzaldehyde a (19 mmol), 4-chlorophenyl boronic acid b (19 mmol), tetrabutylammonium iodide (0.19 mmol), potassium carbonate (57 mmol) and palladium acetate (0.12 mmol) in mixture of acetone/water (25 ml/25 ml) was stirred at 40° C. for 30 mins. The mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting residue was applied to silica chromatography gradient eluting with 100% petroleum ether to 5% ethyl acetate/petroleum ether to yield intermediate c 4′-chloro-biphenyl-2-carbaldehyde as a colourless oil (76%). 1H NMR (300 MHz, CDCl3) δ 9.96 (1H, s), 8.02 (1H, dd, J 7.8 and 1.0 Hz), 7.64-7.30 (7H, m, ArH).

Provenance & Evidence