2,5-Dichlorothiophene → 2,5-Dichlorothiophene-3-sulfonyl chloride

HRID 616727

Reaction equation

HRID 616727 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:7])=[CH:5][CH:6]=1.C(=O)=O.CC(C)=O.[Cl:15][S:16](O)(=[O:18])=[O:17]>>[Cl:1][C:2]1[S:3][C:4]([Cl:7])=[CH:5][C:6]=1[S:16]([Cl:15])(=[O:18])=[O:17]

Participants

4

Reactant 3

HCID 185012,5-DichlorothiopheneHCID 24638Chlorosulfonic acidHCID 18522661Acetone cardice

Product 1

HCID 27360942,5-Dichlorothiophene-3-sulfonyl chloride

Conditions

Temperature
50 °C

Procedure

A 96.8-g (0.632 mol) sample of 2,5-dichlorothiophene was added dropwise to a cooled (dry ice/acetone bath, about -10° to -15° C.) and stirred solution of 163 g (1.39 mol) of chlorosulfonic acid. After the addition was completed, the reaction mixture was stirred at 50° C for 2 hours, cooled, and then poured into 200 g of ice. The aqueous reaction mixture was extracted with methylene chloride. The methylene chloride extract was washed with saturated aqueous sodium bicarbonate solution, washed with water, dried over magnesium sulfate, and evaporated to give 87 g of 2,5-dichloro-3-thienylsulfonyl chloride.

Workup

  1. additionAfter the addition
  2. temperaturecooled
  3. extractionThe aqueous reaction mixture was extracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washwas washed with saturated aqueous sodium bicarbonate solution
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-202c4b75f6e242a8ae686f3407338284
Source dataset
uspto-grants-1978_02
Patent number
US04075347

Linked notes

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