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

HRID 1973154

Reaction equation

HRID 1973154 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-0b35371745844249b70a345e40328c89
Source dataset
uspto-grants-1976_12
Patent number
US03996243

Linked notes

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