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

HRID 42366Notes

Reaction equation

HRID 42366 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+].[CH2:16]1COCC1.IC>C(Cl)Cl.O>[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

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 59251623[4-Bromo-2-(methanesulfonyl)phenyl]methanol

Product 1

HCID 671621004-Bromo-1-(methoxymethyl)-2-(methylsulfonyl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-bromo-2-methansulfonyl-phenyl)-methanol (0.73 g, 2.78 mmol), sodium hydride (0.030 g, 8.4 mmol), and THF (10 mL) was added iodomethane (0.21 mL, 3.36 mmol). After 1 h, the reaction was poured into water (40 mL), diluted in CH2Cl2, and washed with brine (40 mL). The organic layer was dried over (Na2SO4), filtered, concentrated and purified by silica gel column chromatography to give 600 mg of 4-bromo-2-methansulfonyl-1-methoxymethyl-benzene.

Workup

  1. washwashed with brine (40 mL)
  2. dry with materialThe organic layer was dried over (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-009dda63e9274e249d3ea5c81a2e6896
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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