Potassium Carbonate → HCID 69327875, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromothiophenol (1.9 g, 10 mmol) and potassium carbonate (1.5 g, 11 mmol) were stirred in acetone (40 ml). Tetrahydrofurfurylbromide (2 g, 12 mmol) was added dropwise, and the mixture was then heated at 45° C. for 2 hours. The mixture was allowed to cool, the insolubles removed by filtration and the filter pad washed with acetone. The volatiles were removed from the filtrate by evaporation to give crude 1-(2-tetrahyrofurylmethylthio)-4-bromobenzene (3.1 g) an oil (m/z 273). This crude product was dissolved in methanol (60 ml) and water (10 ml). Oxone (8 g) added in portions and the mixture stirred for 2.5 hours. Water (20 ml) was added and the methanol was removed by evaporation. Further water (20 ml) was added to the aqueous residue, which was then extracted with DCM (2×50 ml). The extracts were combined, washed with brine (15 ml), dried and the solvent evaporated. The residue was purified by chromatography on silica eluting with DCM/isohexane/EtOAc (10:8:2) to give the title compound (1.7 g, 56%) as a solid. NMR (CDCl3): 1.56 (m, 1H), 1.88 (m, 2H), 2.13 (m, 1H), 3.20 (dd, 1H), 3.39 (dd, 1H), 3.72 (m, 2H), 4.26 (m, 1H), 7.68 (d, 2H), 7.79 (d, 2H); m/z 305.

Provenance & Evidence