Water → 4-Bromo-1-(methanesulfonyl)-2-(methylsulfanyl)benzene

HRID 732835Notes

Reaction equation

HRID 732835 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4](F)[CH:3]=1.CN(C=O)C.[CH3:18][S-:19].[Na+].O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([S:19][CH3:18])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 459337204-Bromo-2-fluoro-1-(methylsulfonyl)benzene

Product 1

HCID 685174084-Bromo-1-(methanesulfonyl)-2-(methylsulfanyl)benzeneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-bromo-2-fluoro-1-methanesulfonyl-benzene (340 mg, 1.34 mmol) into DMF (8 mL) and treat with sodium thiomethoxide (103 mg, 9.8 mmol). Stir at room temperature for 2 days. Add water (10 mL) and CH2Cl2 (20 mL). Separate the layers and wash the organic layer with aqueous lithium chloride (10%), then dry (magnesium sulfate) and evaporate in vacuo. Chromatograph the residue on a SiO2 column eluting with EtOAc (20%) in hexane to give 286 mg (76%) of the title compound.

Workup

  1. customSeparate the layers
  2. washwash the organic layer with aqueous lithium chloride (10%)
  3. dry with materialdry (magnesium sulfate)
  4. customevaporate in vacuo
  5. washChromatograph the residue on a SiO2 column eluting with EtOAc (20%) in hexane

Sources & evidence

ORD record
ord-f557963689314c48bca3b55b1e95574e
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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