Methyl iodide → 2-Bromo-1-methoxy-4-(methylsulfonyl)benzene

HRID 1406288Notes

Reaction equation

HRID 1406288 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:12].[C:13]([O-])([O-])=O.[K+].[K+].CI.CCOC(C)=O>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 187826382-Bromo-4-(methylsulfonyl)phenol

Product 1

HCID 187826552-Bromo-1-methoxy-4-(methylsulfonyl)benzeneYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-4-(methylsulfonyl)phenol (243 mg, 0.968 mmol) and K2CO3 (201 mg, 1.45 mmol) in DMF (2 mL) was added CH3I (0.0660 mL, 1.06 mmol). The reaction was stirred at room temperature for overnight, diluted reaction with EtOAc (10 mL) and water (10 mL). The organic layer was separated, and the aqueous layer extracted again with EtOAc (15 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, concentrated, and purified with a silica gel column by ISCO CombiFlash® chromatography eluting with 10%-40% EtOAc/Heptane to afford the desired product (168 mg, 65.5%) as a white solid.

Workup

  1. additiondiluted
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted again with EtOAc (15 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified with a silica gel column by ISCO CombiFlash® chromatography
  9. washeluting with 10%-40% EtOAc/Heptane

Sources & evidence

ORD record
ord-c0b934ee1248488b98654487d38836f3
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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