Water → 4-Bromo-1-(methoxymethyl)-2-(methylsulfonyl)benzene

HRID 1406311Notes

Reaction equation

HRID 1406311 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1.[H-].[Na+].[CH3:16]I.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH3:16])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59251623[4-Bromo-2-(methanesulfonyl)phenyl]methanol

Product 1

HCID 671621004-Bromo-1-(methoxymethyl)-2-(methylsulfonyl)benzeneYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-bromo-2-methanesulfonyl-phenyl)-methanol (preparation 112) (500 mg, 1.89 mmol) in DMF (10 mL) was added NaH (226 mg, 5.66 mmol, 60% in oil) at room temperature. After stirring at room temperature for 30 minutes, to above mixture was added MeI (230 mg, 10 mmol) at room temperature. The resulting mixture was stirred at room temperature for 3 hrs. TLC (petroleum ether:EtOAc 1:1) showed the reaction was complete. Then the mixture was poured into H2O (10 mL) and extracted with EtOAc (50 mL×3), washed with brine (10 mL×3), dried over sodium sulfate, concentrated in vacuo to give the residue, which was purified by a Biotage silica gel cartridge (petroleum ether/EtOAc 1:1, Rf˜0.5) to give the title compound (200 mg, 40%) as yellow oil.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 hrs
  2. extractionextracted with EtOAc (50 mL×3)
  3. washwashed with brine (10 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give the residue, which
  7. customwas purified by a Biotage silica gel cartridge (petroleum ether/EtOAc 1:1, Rf˜0.5)

Sources & evidence

ORD record
ord-a762a94742374bc8abcccaeaf2afb250
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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