Dimethylformamide → Ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate

HRID 370984Notes

Reaction equation

HRID 370984 reaction equation
[C:1]([C:4]1[S:8][C:7]2[C:9]([Cl:15])=[C:10]([Cl:14])[C:11]([OH:13])=[CH:12][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][O:13][C:11]1[C:10]([Cl:14])=[C:9]([Cl:15])[C:7]2[S:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]=2[CH:12]=1)[CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 132900362-Acetyl-6,7-dichloro-5-hydroxybenzo[b]thiophene

Product 1

HCID 53636860Ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetateYield 42.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a solution of 9.0 g of 2-acetyl-6,7-dichloro-5-hydroxybenzo[b]thiophene and 200 ml of 2-butanone is added a solution of 6.62 g of ethyl bromoacetate in 50 ml of 2-butanone, 5.2 g of potassium carbonate and 2.2 ml of dimethylformamide. The reaction mixture is heated under reflux for 2 hrs, allowed to cool and filtered. The filtrate is extracted with ether (3 times). The layers are separated and the organic phase is washed with water, saturated sodium chloride solution, dried and filtered. The filtrate is evaporated. The residue is dissolved in dichloromethane and chromatographed on alumina, using dichloromethane as the eluant. Evaporation of the eluant gives 5.1 g of ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 hrs
  3. temperatureto cool
  4. filtrationfiltered
  5. extractionThe filtrate is extracted with ether (3 times)
  6. customThe layers are separated
  7. washthe organic phase is washed with water, saturated sodium chloride solution
  8. customdried
  9. filtrationfiltered
  10. customThe filtrate is evaporated
  11. dissolutionThe residue is dissolved in dichloromethane
  12. customchromatographed on alumina
  13. customEvaporation of the eluant

Sources & evidence

ORD record
ord-0bf20c0f6a074e1d873e012dd1a2c661
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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