Dimethylformamide → 2-(4-Chloro-3-nitrobenzenesulfonyl)ethanol

HRID 1649709Notes

Reaction equation

HRID 1649709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][OH:23].CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:21][CH2:22][OH:23])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 40975444-Chloro-3-nitrobenzenesulfinic acid

Product 1

HCID 136852842-(4-Chloro-3-nitrobenzenesulfonyl)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40 g of 4-Chloro-3-nitrobenzenesulfinic acid, 27.8 g of potassium carbonate, 24.8 g of 2-bromoethanol and 200 ml of dimethylformamide were mixed together and reacted at 50° C. for a period of 8 hours. The reaction mixture was then poured into of water and extracted with ethyl acetate. The organic layer was recovered and the solvent was removed by distillation under reduced pressure. The oily residue was refined using silica gel short-column chromatography to obtain an oily product.

Workup

  1. customreacted at 50° C. for a period of 8 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was recovered
  4. customthe solvent was removed by distillation under reduced pressure
  5. customto obtain an oily product

Sources & evidence

ORD record
ord-a12216c2d5ed4ab78283d607b3743ae7
Source dataset
uspto-grants-1990_05
Patent number
US04921785

Reaction notes

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