Sulfuryl chloride → Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate

HRID 1200099Notes

Reaction equation

HRID 1200099 reaction equation
S(Cl)([Cl:4])(=O)=O.[OH:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13]>C(Cl)(Cl)Cl>[Cl:4][C:8]1([C:12]([O:14][CH3:15])=[O:13])[C:7](=[O:6])[CH:11]=[CH:10][S:9]1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 5811273-Hydroxy-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sulphuryl chloride (0.11 mol) was added to a stirred solution of methyl 3-hydroxythiophene-2-carboxylate (0.1 mol) (C. Corral, J. Lissavetzty; Syntheses (1984), 847) in anhydrous chloroform (50 ml). After stirring at room temperature for 4 hours the solvent was removed under reduced pressure and the residue used crude in the following preparations (m.p. 70°-71° C., hexane).

Workup

  1. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-c016b875267347e2bb1edf2a3d93ad84
Source dataset
uspto-grants-1990_02
Patent number
US04904686

Reaction notes

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