Dimethyl Sulfoxide → HCID 69412700, compound

Participants

Reaction Steps

A capped scintillation vial containing a mixture of 158 mg (1.0 mmol) of 3,4-difluorobenzoic acid, 186 μL (2.0 mmol) of 2-propanethiol and 652 mg (2.0 mmol) of cesium carbonate in 2.5 mL of DMSO was heated at 50 C for 2.5 days. The reaction mixture was cooled to room temperature and partitioned between ethyl ether and 1M HCl. The organic phase was separated and washed with water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The concentrated material was dissolved in 6 mL of THF and treated with a solution of 0.52 g (2.0 mmol) of 3-chloroperoxybenzoic acid (66% by weight) in 4 mL of DCM. The reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was dissolved in 5% methanol/CHCl3 and absorbed onto SiO2. Chromatography on SiO2 (5% to 7% methanol/CHCl3) afforded 204 mg (83% yield) of 3-fluoro-4-(propane-2-sulfonyl)-benzoic acid as a white solid.

Provenance & Evidence