Ethyl Acetate → (4-Bromo-3,5-dimethoxyphenyl)methanol

HRID 2267195Notes

Reaction equation

HRID 2267195 reaction equation
[Br:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[O:14][CH3:15].[BH4-].[Li+].C(OCC)(=O)C>O1CCCC1>[Br:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:14][CH3:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 117713Methyl 4-bromo-3,5-dimethoxybenzoateHCID 4148881Lithium borohydride

Product 1

HCID 11149289(4-Bromo-3,5-dimethoxyphenyl)methanolYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-bromo-3,5-dimethoxybenzoate (133.2 g) in tetrahydrofuran (500 mL) was added lithium borohydride (20.8 g) slowly at room temperature, and the mixture was further stirred for 3 hours under reflux with heating. The reaction mixture was cooled down to room temperature, and ice water (1.5 L) and ethyl acetate (1.2 L) were added, and extraction with ethyl acetate was performed. The resultant organic layer was washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain 118.8 g of a title compound as white solid.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. extractionextraction with ethyl acetate
  4. washThe resultant organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1eebac674076400791465f1c3a853e94
Source dataset
uspto-grants-2010_12
Patent number
US07858809B2

Reaction notes

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