Potassium Hydroxide → HCID 10640226, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromothiophenol (100 g; 0.53 mole) and potassium hydroxide (29.5 g; 0.53 mole) in ethanol (1000 mL) was stirred until all material had dissolved. t-Butyl 2-bromoisobutyrate (117.6 g; 0.53 mole) was added dropwise over 30 min, keeping the temperature below 55° C. The resulting mixture was heated at reflux for 1 h, then cooled to 23° C. The precipitate (KBr) was removed by filtration and the solvent evaporated. The residue was partitioned between water (1000 mL) and methylene chloride (500 mL) and the organic layer was separated, dried (Na2SO4) and evaporated to afford a white solid. Crystallization from hexane gave a white solid (119.85 g; 68%).

Provenance & Evidence