Sodium methanethiolate → 5-Chloro-2-methylsulfanylindan-1-one

HRID 2119671Notes

Reaction equation

HRID 2119671 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].[CH3:13][S-:14].[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:14][CH3:13])[CH2:10]2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 113340692-Bromo-5-chloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 99207715-Chloro-2-methylsulfanylindan-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.98 g (4 mmol) of 2-bromo-5-chloroindan-1-one and 0.42 g (6 mmol) of sodium thiomethoxide are suspended in 5 ml of ethanol, treated in an ultrasonic bath for 30 minutes and then stirred at room temperature for 90 minutes. The reaction mixture is concentrated under reduced pressure and chromatographed on silica gel using toluene/ethyl acetate 10/1. The eluates are concentrated under reduced pressure, giving 0.63 g of 5-chloro-2-methylsulfanylindan-1-one of melting point 90° C.

Workup

  1. additiontreated in an ultrasonic bath for 30 minutes
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customchromatographed on silica gel
  4. concentrationThe eluates are concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4a2e66066de45bf96959c0bb191055f
Source dataset
uspto-grants-2004_02
Patent number
US06686397B2

Reaction notes

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