Hydrochloric Acid → 4-(Benzyloxy)-3-bromobenzaldehyde

Participants

Reaction Steps

3-Bromo-4-hydroxy-benzaldehyde (1.9 g, 9.45 mmol) was added slowly, at 0° C., to a suspension of NaH 95% (290 mg, 11.34 nol) in dry N,N-dimethylformamide (45 mL). The mixture was stirred for 0.5 hours. Benzyl chloride (1.3 mL, 11.34 mmol) was added and the reaction stirred at room temperature overnight. 1N HCl (40 mL) was added and the layers separated. The aqueous layer was extracted with diethyl ether (5×50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under vacuum. The residue was chromatographed (silica gel, hexanes/ethyl acetate 9:1) to produce 4-Benzyloxy-3-bromo-benzaldehyde as a white solid (2.47 g, 90%). 1H-NMR (CDCl3, 200.15 MHz): δ 9.82 (s, 1H), 8.09 (d, 1H, J=1.8), 7.76 (dd, 1H, J=8.4, 1.8), 7.47–7.32 (m, 5H), 7.02 (d, 1H, J=8.4), 5.24 (s, 2H.

Provenance & Evidence