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

HRID 2358286Notes

Reaction equation

HRID 2358286 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-one

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 were 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 was concentrated under reduced pressure and chromatographed on silica gel using toluene/ethyl acetate 10/1. The eluates were concentrated under reduced pressure, giving 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 was concentrated under reduced pressure
  3. customchromatographed on silica gel
  4. concentrationThe eluates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-d39acb2e2f494fca9dfc2b80aa046037
Source dataset
uspto-grants-2010_07
Patent number
US07763662B2

Reaction notes

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