Methyl iodide → 4-Bromo-2-(methanesulfonyl)-1-methoxybenzene

HRID 42356Notes

Reaction equation

HRID 42356 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([S:8]([O-:10])=[O:9])[CH:7]=1.[Na+].I[CH3:15]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([S:8]([CH3:15])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 67162120Sodium 5-bromo-2-methoxybenzenesulfinate

Product 1

HCID 223451764-Bromo-2-(methanesulfonyl)-1-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium 5-bromo-2-methoxybenzenesulfinate (1.99 g) in DMF (873 ml) was added iodomethane (32 ml). The reaction mixture turned yellow and was stirred at room temperature for 2 hours. The reaction was quenched by the addition of water (ca. 5 ml). The mixture was diluted with EtOAc and extracted with 5% LiCl (3×) and brine (1×). The organic layer was dried (Na2SO4/MgSO4) and filtered. The filtrate was concentrated and purified by silica gel column chromatography to give 1.62 g 4-bromo-1-methoxy-2-(methylsulfonyl)benzene as a white crystalline solid.

Workup

  1. customThe reaction was quenched by the addition of water (ca. 5 ml)
  2. additionThe mixture was diluted with EtOAc
  3. extractionextracted with 5% LiCl (3×) and brine (1×)
  4. dry with materialThe organic layer was dried (Na2SO4/MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2c1f948fe58347f086675ea6bc4455e5
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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