1,4-Dibromobutane → 3a,4,7,7a-Tetrahydro-2-[4-bromobutyl]-4,7-ethano-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Participants

Reaction Steps

A solution of 456 mg (19 mmol) of sodium hydride (prepared from 760 mg of 60% sodium hydride in mineral oil by pentane wash) in 40 ml of dimethylformamide is treated portionwise with 4.05 g (19 mmol) of 3a,4,7,7a-tetrahydro-4,7-ethano-1,2-benzisothiazol-3(2H)-one-1,1-dioxide at 0° C. The resulting solution is added dropwise to a solution of 12.3 g (57 mmol) of 1,4-dibromobutane in 40 ml of dimethylformamide. The mixture is maintained with stirring at room temperature for 22.5 hours. The solvent is removed under high vacuum and the residue partitioned between methylene chloride and water. The combined methylene chloride extracts are washed with brine and dried over MgSO4. Filtration and removal of solvent in vacuo gives an oily solid which is triturated with ethyl ether and filtered to give 1.05 g of the title compound, mp 118°-122° C.

Provenance & Evidence