Sodium benzenethiolate → 5-chloro-2-phenylsulfanylindan-1-one

HRID 496695Notes

Reaction equation

HRID 496695 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:11])[CH:8]=2)[C:3]1=[O:12].[S-:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+]>C(O)C>[Cl:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3](=[O:12])[CH:2]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10]2

Participants

4

Reactant 2

HCID 4110039Sodium benzenethiolateHCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 98141425-chloro-2-phenylsulfanylindan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g of 2-bromo-5-chloroindan-1-one and 2.8 g of sodium thiophenoxide was suspended in 30 ml of ethanol and heated under reflux for 3 h. The cooled reaction mixture was concentrated and purified chromatographically on silica gel using toluene/ethyl acetate 10/1. This gave 5-chloro-2-phenylsulfanylindan-1-one of melting point 89° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated
  5. custompurified chromatographically on silica gel

Sources & evidence

ORD record
ord-e973d3ecbaa8421c88b7e62ade7ad637
Source dataset
uspto-grants-2005_09
Patent number
US06946492B2

Reaction notes

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