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

HRID 1884082Notes

Reaction equation

HRID 1884082 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 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 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 was concentrated under reduced pressure
  3. customchromatographed on silica gel
  4. concentrationThe eluates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4d193b4217d439d96e8d6adc58e6cff
Source dataset
uspto-grants-2004_07
Patent number
US06762326B2

Reaction notes

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