Methane, dichloromethoxy- → 7-Fluoro-2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde

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Reaction Steps

A solution of 6-fluoro-2,3-dihydro-benzo[1,4]dioxine (prepared from 6-amino-2,3-dihydro-benzo[1,4]dioxine according to the procedure of V. Daukas, P. Gaidelis, R. Martinkus, S. Urboniene, Chemija, 1999, 10 (1), 59), (154 mg, 1 mmol) in dichloromethane (0.5 ml) was treated with dichloromethyl methyl ether (0.25 ml) at 0° C. under argon. Titanium tetrachloride (0.45 ml) in dichloromethane (0.5 ml) was added over 0.25 hours. The cooling bath was removed and the mixture was stirred at ambient temperature for 1 hour before being quenched with water and extracted with ether. The ether extract was washed with aqueous sodium bicarbonate and brine. Drying and evaporation afforded a brown oil which was purified by chromatography on silica (ethyl acetate/hexane) affording a clear oil (0.12 g).

Provenance & Evidence