1,4-Dioxane → 1,1'-(5,5-Dioxidodibenzo[b,d]thiophene-3,7-diyl)diethanone

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,7-dibromodibenzo[b,d]thiophene 5,5-dioxide (600 mg, 1.604 mmol), Tributyl(1-ethoxyvinyl)tin (2.251 mL, 6.67 mmol) and Pd(Ph3P)4 (185 mg, 0.160 mmol) in 1,4-dioxane (15 mL) were degassed with nitrogen for 10 min then it was heated at 90° C. for overnight under nitrogen. The reaction mixture was cooled to room temperature and 15 mL of 10% HCl was added then stirred for 1 h. The mixture was extracted with ethyl acetate and the organic layer was washed with water and brine. The organics were dried (Na2SO4) and concentrated. The crude material was purified on silica gel using 0-100% ethyl acetate in hexane. The desired fractions were concentrated to give a white solid.

Provenance & Evidence