Sulfuryl chloride → HCID 19918030, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9.6 g (40 mmol) of methyl 3-bromo-4,5-dihydroxybenzoate, 8.4 g (62 mmol) of sulphuryl chloride and 400 ml of glacial acetic acid is stirred at 55° C. for 60 hours and subsequently concentrated at 40° C. in a vacuum. The residue is dissolved in 200 ml of methanol and saturated with hydrogen chloride. After standing at room temperature for 5 hours the solvent is distilled off in a vacuum. The residual material is treated with about 100 ml of dichloromethane/ethyl acetate/petroleum ether (1:1:1 v/v) and filtered. The filtrate is concentrated and the residue is crystallized and recrystallized from diethyl ether/petroleum ether. There are obtained 3.4 g of methyl 5-bromo-2-chloro-3,4-dihydroxybenzoate as white crystals of melting point 103° C.

Provenance & Evidence