Thiophenol → 3-Chloropropyl phenyl sulfide

HRID 1832258Notes

Reaction equation

HRID 1832258 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH2:10][CH2:11][Cl:12].C1COCC1>O>[Cl:12][CH2:11][CH2:10][CH2:9][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 80061-Bromo-3-chloropropaneHCID 8028Tetrahydrofuran

Product 1

HCID 2696063-Chloropropyl phenyl sulfideYield 112.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of benzenethiol (0.550 g, 5.00 mmol), 1-bromo-3-chloropropane (106 mg, 5.50 mmol), TEA (1.01 g, 10.0 mmol) and THF (10.0 mL) was stirred for 12 h at 25° C. The resulting crude mixture was diluted with water (40 mL), the aqueous layer was extracted with CH2Cl2 (3×30 mL). The combined organic layers were concentrated in vacuo and the residue was purified by preparative TLC using hexane:EtOAc (10:1) to give the desired product [(3-chloropropyl)sulfanyl]benzene (1.05 g, 100%).

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (3×30 mL)
  2. concentrationThe combined organic layers were concentrated in vacuo
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-d77b1ec3aaf64cde841984d71d0168e4
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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