Methane, dichloromethoxy- → 6-fluorochroman-8-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

13.74 g (90.28 mmol) of 6-fluorochroman are dissolved in 250 ml of methylene chloride. The whole is cooled to 0° C. and 20.15 ml (0.18 mol) of TiCl4 are added dropwise. The solution becomes brown and is stirred for 10 minutes at room temperature. 8.78 ml (99.3 mmol) of α,α-dichloromethyl ether are then introduced. The whole is stirred overnight at room temperature, poured into ice-cold water and decanted. The organic phase is dried and evaporated to yield 17.7 g of a residue which is purified by chromatography on silica (eluant CH2Cl2 /cyclohexane: 50/50). 6.3 g of the expected product are obtained. Yield: 38.7%.

Provenance & Evidence