Thionyl Chloride → HCID 21202943, compound

Participants

Reaction Steps

Thionyl chloride (5 ml, 70 mmol) is added at ambient temperature to 3-bromophenoxyacetic acid (5.77 g, 25 mmol). The reaction mixture is brought to reflux for 2 hours. After returning to ambient temperature, it evaporates and the acid chloride is used. The 3-bromophenoxyacetyl chloride previously obtained is dissolved in dichloromethane (150 ml) and added to a solution of aluminum chloride (6.7 g, 50 mmol) in 50 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 30 minutes and then poured into a an equal volume water-ice mixture (400 ml). The mixture is extracted with dichloromethane, dried over MgSO4 filtered and evaporated. The raw product is purified by flash chromatography on silica (eluent petroleum ether ether=100:10). 0.96 g of 6-bromo-3-coumarone is obtained (yield=18%) of formula:

Provenance & Evidence