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

HRID 2253399Notes

Reaction equation

HRID 2253399 reaction equation
S(Cl)(C)(=O)=O.[Br:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH2:15][OH:16])=[CH:9][C:8]=1[O:17][CH3:18].[CH2:19](N(CC)CC)C.C[O-].[Na+].CO>COCCOC.O.C1(C)C=CC=CC=1>[Br:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH2:15][O:16][CH3:19])=[CH:9][C:8]=1[O:17][CH3:18]

Participants

9

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10942334Sodium MethoxideHCID 11149289(4-Bromo-3,5-dimethoxyphenyl)methanol

Product 1

HCID 230809402-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzeneYield 99.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Mesyl chloride (34.5 mL, 446 mmol) was added to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (100 g, 405 mmol) and triethylamine (67.5 mL, 484 mmol) in 1,2-dimethoxyethane (1000 mL) while cooling with ice, and the reaction mixture was stirred for 30 minutes. After adding a 28% sodium methoxide in methanol (350 mL, 1.72 mol) to the reaction mixture, it was further stirred for 3 hours at room temperature. Upon completion of the reaction, toluene (1000 mL) and water (1000 mL) were added to the reaction mixture, the aqueous layer was removed, and the organic extract was washed with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL) in that order and concentrated under reduced pressure to afford 105 g of the title compound as a colorless oil (99.5% yield).

Workup

  1. temperaturewhile cooling with ice
  2. stirringwas further stirred for 3 hours at room temperature
  3. additionwere added to the reaction mixture
  4. customthe aqueous layer was removed
  5. extractionthe organic extract
  6. washwas washed with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL) in that order
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-581fa21972a34291bf12ca933a48f668
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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