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

HRID 2253401Notes

Reaction equation

HRID 2253401 reaction equation
[BH4-].[Li+].[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:7]([C:8](OC)=[O:9])=[CH:6][C:5]=1[O:16][CH3:17].C(OCC)(=O)C>O1CCCC1>[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[O:16][CH3:17]

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

Lithium borohydride (20.8 g) was slowly added to a solution of methyl 4-bromo-3,5-dimethoxybenzoate (133.2 g) in tetrahydrofuran (500 mL) at room temperature, and the mixture was stirred for 3 hours while heating to reflux. The reaction mixture was cooled to room temperature, ice water (1.5 L) was added, and then ethyl acetate (1.2 L) was further added for extraction. The obtained organic extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to afford the title compound (118.8 g) as a white solid.

Workup

  1. temperaturewhile heating to reflux
  2. extractionThe obtained organic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf6e216cd21e4aa6a522c7bd7a21ac6b
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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