Methyl iodide → 2-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene

HRID 2253402Notes

Reaction equation

HRID 2253402 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([CH2:12][OH:13])=[CH:6][C:5]=1[O:14][CH3:15].IC.[C:18](OCC)(=O)C>CN(C)C=O>[Br:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([CH2:12][O:13][CH3:18])=[CH:6][C:5]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11149289(4-Bromo-3,5-dimethoxyphenyl)methanol

Product 1

HCID 230809402-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil; 24.7 g) was added to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (118.8 g) in N,N-dimethylformamide (960 mL) while cooling with ice, and after stirring for 10 minutes, iodomethane (41.7 mL) was added dropwise, the temperature was increased to room temperature and stirring was continued for 1 hour. The obtained reaction mixture was poured into ice water (2.5 L), extraction was performed with ethyl acetate, the extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and the title compound (121.3 g) was obtained as a colorless oil from the n-hexane:ethyl acetate (4:1) fraction.

Workup

  1. temperaturewhile cooling with ice
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. customThe obtained reaction mixture
  5. washthe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9611bc61c2bf4609a9047e035150afa1
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

Loading…