Toluene → HCID 86715129, compound

Participants

Reaction Steps

To a solution of 3-bromo-2-fluorobenzoic acid (15 g) in toluene (200 mL) was added SOCl2 (12.2 g) at r.t. and the suspension was heated to reflux with stirring for 2.5 h. The volatiles were removed under reduced pressure. The residue was taken up in DCM (20 mL) and added to a solution of AlCl3 (9.1 g) in dichloroethane at 10-20° C. Ethylene was bubbled through the solution for 4 hours after which the resulting mixture was stirred for 15 hours and then quenched with 4 N HCl (100 mL). The resulting layers were separated and the aqueous phase was extracted with DCM (100 mL×3). The combined organic layers were washed with water (50 mL×3), brine (50 mL) and dried over Na2SO4. After filtration, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: DCM/PE 1:200) to provide the subtitle compound. MS ESI+: m/z=265 [M+H]+.

Provenance & Evidence