Dichloromethane → 2-n-Butyl-3-(4-methoxyphenylsulfonyl)benzofuran

Participants

Reaction Steps

To a solution of 4.35 g. (0.025 mol.) of 2-n-butylbenzofuran in 25 ml. of methylene chloride was added a solution of 5.16 g. (0.025 mol.) of 4-methoxybenzenesulfonyl chloride in 50 ml. of methylene chloride. The resulting solution was cooled to 0° and 6.9 g. (0.026 mol.) of stannic chloride was added dropwise. The reaction mixture was stirred for 30 minutes in the cold, for 1.5 hours at ambient temperature, then refluxed for ca. 60 hours. The mixture was poured into 200 ml. of water and stirred for 5 minutes. The layers were separated and the organic phase was extracted three times with water. Sodium hydroxide solution (ca. 1%) was added to the organic layer and it was stirred at ambient temperature for 1 hour. The layers were separated and the organic phase was washed three times with water and once with a saturated sodium chloride solution, dried (MgSO4) and evaporated to dryness to give a residue which was chromatographed on a silica gel "dry column" with 9:1 methylene chloride-ether as eluant to give 2-n-butyl-3-(4-methoxyphenylsulfonyl)benzofuran.

Provenance & Evidence