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

HRID 1764660Notes

Reaction equation

HRID 1764660 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].C(Cl)Cl.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O>[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[C:9]=1[S:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 74014-Methoxybenzenesulfonyl chlorideHCID 779512-Butylbenzofuran

Product 1

HCID 227689052-n-Butyl-3-(4-methoxyphenylsulfonyl)benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. temperatureThe resulting solution was cooled to 0°
  2. temperaturerefluxed for ca. 60 hours
  3. additionThe mixture was poured into 200 ml
  4. customThe layers were separated
  5. extractionthe organic phase was extracted three times with water
  6. additionSodium hydroxide solution (ca. 1%) was added to the organic layer and it
  7. stirringwas stirred at ambient temperature for 1 hour
  8. customThe layers were separated
  9. washthe organic phase was washed three times with water
  10. dry with materialonce with a saturated sodium chloride solution, dried (MgSO4)
  11. customevaporated to dryness
  12. customto give a residue which
  13. customwas chromatographed on a silica gel "
  14. dry with materialdry column" with 9:1 methylene chloride-ether as eluant

Sources & evidence

ORD record
ord-15f42a9abeae4c57a99ea55bd38f1e52
Source dataset
uspto-grants-1978_09
Patent number
US04117128

Reaction notes

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