1-Bromo-3-chloropropane → HCID 13749597, compound

HRID 867904Notes

Reaction equation

HRID 867904 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].Br[CH2:11][CH2:12][CH2:13][Cl:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:14][CH2:13][CH2:12][CH2:11][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1382782-Mercaptobenzenemethanol

Product 1

HCID 13749597HCID 13749597, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11.9 g of 2-(hydroxymethyl)thiophenol, 35.44 g of 1-bromo-3-chloropropane, 11.58 g of potassium carbonate and 150 ml of dimethylformamide is stirred at room temperature for 2 hours. Insoluble materials are filtered off, and the filtrate is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is distilled under reduced pressure. 16.8 g of 2-(3-chloropropylthio)benzylalcohol are obtained as colorless oil. Yield: 93%.

Workup

  1. filtrationInsoluble materials are filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customto remove solvent
  4. additionWater is added to the residue
  5. extractionthe aqueous mixture is extracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-7bc04f53405a4c9e8ca89b143c83fcae
Source dataset
uspto-grants-1988_10
Patent number
US04777178

Reaction notes

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