tert-Butyl methyl ether → (4-Bromo-3-fluorophenyl)(cyclopropyl)sulfane

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-bromo-3-fluorobenzenethiol (Preparation 26, 400 mg, 1.93 mmol), potassium tert-butoxide (238 mg, 2.12 mmol) and bromocyclopropane (701 mg, 5.80 mmol) in DMSO (10 mL) was heated at 90° C. for 16 hours. Additional potassium tert-butoxide (43 mg, 0.386 mmol) and bromocyclopropane (467 mg, 3.86 mmol) were added and heating continued at 90° C. for 30 hours. The mixture was cooled to room temperature and poured into 2-methoxy-2-methylpropane (30 mL). The mixture was washed with water (2×30 mL), dried over Na2SO4, concentrated in vacuo and purified by silica gel column chromatography eluting with heptanes to give the title compound as a colourless oil 27% yield, 130 mg.

Provenance & Evidence