Sulfuryl chloride → 3-Chloro-2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester

HRID 2413232Notes

Reaction equation

HRID 2413232 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

HCID 24648Sulfuryl chlorideHCID 136630372-Methylbenzo[b]thiophene-5-carboxylic acid methyl ester

Product 1

HCID 136630443-Chloro-2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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°.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was crystallised from methanol/water

Sources & evidence

ORD record
ord-303769ecf52749dcbe676936c33968cf
Source dataset
uspto-grants-1985_01
Patent number
US04496572

Reaction notes

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