Thionyl Chloride → 2-Ethyl-3-chlorocarbonyl-benzo[b]thiophene

HRID 436007Notes

Reaction equation

HRID 436007 reaction equation
[CH2:1]([C:3]1[S:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[C:4]=1[C:12]([OH:14])=O)[CH3:2].S(Cl)([Cl:17])=O>>[CH2:1]([C:3]1[S:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[C:4]=1[C:12]([Cl:17])=[O:14])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 214550892-Ethyl-3-carboxy-benzo[b]thiophene

Product 1

HCID 214550652-Ethyl-3-chlorocarbonyl-benzo[b]thiopheneYield 91%

Procedure

Into a quarter-litre flask equipped with a condenser were introduced 27.2 g (0.128 mol) of 2-ethyl-3-carboxy-benzo[b]thiophene and 100 ml of thionyl chloride. The solution was refluxed for 3 hours and the excess of thionyl chloride was then eliminated by distillation. The residue was distilled and 27.1 g of 2-ethyl-3-chlorocarbonyl-benzo[b]thiophene were obtained representing a yield of 91%; b.p. 110/120° C (0.05 mm/Hg).

Workup

  1. customInto a quarter-litre flask equipped with a condenser
  2. temperatureThe solution was refluxed for 3 hours
  3. distillationthe excess of thionyl chloride was then eliminated by distillation
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-558a78ba99d5442792c83a907a736ee9
Source dataset
uspto-grants-1977_02
Patent number
US04007204

Reaction notes

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