Potassium Phosphate, Tribasic → 7-{4-[(6-Bromohexyl)oxy]butyl}thiochromane 1,1-dioxide

Participants

Reaction Steps

To a solution of 4-[(6-bromohexyl)oxy]but-1-ene (180 mg) in tetrahydrofuran (0.6 ml) was added a 0.5M solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (1.8 ml). The solution was stirred at room temperature, under nitrogen for 2 h. Tripotassium phosphate (324 mg) in water (0.46 ml) was added, followed by 7-bromothiochromane 1,1-dioxide (200 mg), palladium (II) acetate (2 mg) and triphenylphosphine (4 mg). The resultant mixture was heated at 60° C. for 17 h. Water was added and the organic layer washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on a Biotage cartridge (40 g) eluting with cyclohexane-ethyl acetate (1:1) to give the title compound (121 mg) LCMS RT=3.66 min

Provenance & Evidence