Sulfuryl chloride → 3-Chloro-2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester
Reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]([C:10]1[CH:19]=[CH:18][C:13]2[S:14][C:15]([CH3:17])=[CH:16][C:12]=2[CH:11]=1)=[O:9]>C(Cl)(Cl)Cl>[CH3:6][O:7][C:8]([C:10]1[CH:19]=[CH:18][C:13]2[S:14][C:15]([CH3:17])=[C:16]([Cl:4])[C:12]=2[CH:11]=1)=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sulphuryl chloride (3.38 g) was added dropwise to a stirred solution of 2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester (5.15 g) in chloroform (50 ml). The resulting solution was heated under reflux for 2 hours, cooled, washed with water, dried (Na2SO4) and evaporated. The residue was crystallised from methanol/water to give 3-chloro-2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester, 3.00 g, m.p. 85°-86°.