Bromochloromethane → 1-((Chloromethyl)sulfonyl)naphthalene

Participants

Reaction Conditions

Reaction Steps

A mixture of naphthalene-1-sulfonyl chloride (10.0 g, 44 mmoles), sodium sulfite (11.12 g, 88 mmoles), and sodium bicarbonate (7.4 g, 88 mmoles) in water (50 mL) was heated to 100° C. for one hour. The crude sodium sulfinate solution was allowed to cool for 30 minutes, and then treated with bromochloromethane (43 mL, 661 mmoles) and tetra-N-butylammonium bromide (1.4 g, 4.4 mmoles). The resultant mixture was heated to 75° C. overnight. All solvents were removed under vacuum. Compound was recrystallized from CH2Cl2/hexane to give the title compound as an off white solid (10.62 g, 44 mmoles).

Provenance & Evidence