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

HRID 347867Notes

Reaction equation

HRID 347867 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-7d0ab1a1cbf748d7937d0646a288b16a
Source dataset
uspto-grants-2007_02
Patent number
US07176216B2

Reaction notes

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