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

HRID 1789365Notes

Reaction equation

HRID 1789365 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 wahsed 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. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove solvent
  9. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-1ab0649934ff468ca3ce4dfc173e5293
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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