Sodium methanethiolate → 4-Bromo-1,2-bis(methylsulfanyl)benzene

HRID 748903Notes

Reaction equation

HRID 748903 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4](F)[CH:3]=1.[CH3:11][S-:12].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([S:12][CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 219340644-Bromo-2-fluorothioanisole

Product 1

HCID 149644854-Bromo-1,2-bis(methylsulfanyl)benzeneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-bromo-2-fluoro-1-methylsulfanyl-benzene (4.8 g, 22 mmol) and sodium methanethiolate (1.6 g, 22 mmol) in DMF (50 mL). Stir for 48 hours. Pour the reaction mixture into ice (10 g). Separate the layers and wash the organic layer with aqueous saturated NaHCO3 and brine. Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting with diethyl ether in hexane (0 to 5%) to give 4.82 g of 4-bromo-1,2-bis-methylsulfanylbenzene (89%).

Workup

  1. customSeparate the layers
  2. washwash the organic layer with aqueous saturated NaHCO3 and brine
  3. dry with materialDry with MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. washChromatograph the residue on a column eluting with diethyl ether in hexane (0 to 5%)

Sources & evidence

ORD record
ord-e75282a6e4ef4725bf465f424c583775
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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