3-Hydroxybenzaldehyde → Benzaldehyde, 3-(4-fluorophenoxy)-

Participants

Reaction Steps

To a mixture of 3-hydroxybenzaldehyde (5.0 g, 40.9 mmol, 1.0 eq) and 4-fluorobromobenzene (14.3 g, 81.7 mmol, 2 eq) in pyridine was added K2CO3 (8.5 g, 61.4 mmol, 1.5 eq) followed by copper powder (1.3 g, 20.5 mmol, 0.5 eq). The reaction mixture was refluxed for 60 h before being filtered to remove the copper powder. The filtrate was then distilled under reduced pressure to remove pyridine. The resultant residue was taken in ethyl acetate and washed with water. The organic layer was dried over anhydrous Na2SO4 and concentrated under in vacuo. The residue was purified by silica gel column chromatography eluting with 10-20% ethyl acetate in hexane to afford the desired compound (3.0 g, 35%). 1H NMR (400 MHz, CDCl3) δ 9.96 (s, 1H), 7.61-7.58 (t, 1H), 7.50-7.48 (t, 1H), 7.42-7.41 (t, 1H), 7.28-7.24 (m, 1H), 7.11-6.99 (m, 4H). MS (ESI): 218.0 (M+H)+.

Provenance & Evidence