Water → HCID 66666627, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl-3-bromo-4-fluoro benzoate (20 g, 86 mmol) and 4-chlorophenol (11.0 g, 171 mmol) in dimethylsulfoxide (500 mL) was added potassium tert-butoxide (19.3 g, 171 mmol) and the reaction mixture was stirred at 120° C. for 16 hours and then poured into 500 mL of water and extracted with dichloromethane (3×100 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified via column chromatography on silica gel (1:1 petroleum ether:EtOAc) to yield 18 g (55 mmol) of 3-bromo-4-(4-chlorophenoxy)-benzoic acid and 2 g of the title compound.

Provenance & Evidence