Methane, dichloromethoxy- → 2-Fluoro-4-hydroxy-5-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-fluoro-2-methylphenol (630 mg, 5 mmol) in dichloromethane (5 ml) was added titanium chloride (1890 mg, 10 mmol) dropwise at 0° C. and then (dichloromethyl)-methyl ether (689 mg, 6 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 hour, quenched with ice (50 g) and extracted with ethyl acetate. The organic layer was separated, dried over Na2SO4, concentrated and applied to a silica gel column, eluting with hexane/ethyl acetate (10:1), to furnish the title compound (545 mg, 71% yield) as a white solid. 1H NMR (270 MHz, CDCl3) δ 2.25 (3H, s), 6.04 (1H, brs), 6.60 (1H, d, J=11.2 Hz), 7.66 (1H, d, J=7.9 Hz), 10.18 (1H, s).

Provenance & Evidence