Sulfuryl chloride → 5-chloro-4-methoxythiophene-3-carboxylic acid

HRID 2050902Notes

Reaction equation

HRID 2050902 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:8]([OH:10])=[O:9])=[CH:5][S:6][CH:7]=1.S(Cl)([Cl:14])(=O)=O>C(Cl)(Cl)Cl>[Cl:14][C:7]1[S:6][CH:5]=[C:4]([C:8]([OH:10])=[O:9])[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 27783794-methoxythiophene-3-carboxylic acid

Product 1

HCID 27783825-chloro-4-methoxythiophene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 4-methoxythiophene-3-carboxylic acid (3.16 g) in chloroform (10 ml) was added freshly distilled sulphuryl chloride (1.8 ml). After the exothermic reaction had subsided the product was extracted into 2N NaOH and washed with chloroform. The aqueous solution was acidified with 2N HCl and extracted into dichloromethane, washed with water, dried over magnesium sulphate and the solvent evaporated. The product was crystallised from dichloromethane/n-hexane.

Workup

  1. customAfter the exothermic reaction
  2. extractionwas extracted into 2N NaOH
  3. washwashed with chloroform
  4. extractionextracted into dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent evaporated
  8. customThe product was crystallised from dichloromethane/n-hexane

Sources & evidence

ORD record
ord-b4722c4db17541b5b4e8e699bd51f4bb
Source dataset
uspto-grants-1991_05
Patent number
US05015656

Reaction notes

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