Methanol → (4-Bromo-3-methoxyphenyl)methanol

HRID 247452Notes

Reaction equation

HRID 247452 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].B.CO>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 13551345(4-Bromo-3-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Bromo-3-methoxybenzoic acid (23.1 g, 0.1 m) dissolved in tetrahydrofuran (200 ml) is added to 1M borane in tetrahydrofuran (150 ml) stirred at 5°. The mixture is refluxed, cooled, treated with methanol, refluxed and concentrated in vacuo to give 4-bromo-3-methoxybenzyl alcohol.

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturecooled
  3. temperaturerefluxed
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d29644f06690430f91044127a92bcee1
Source dataset
uspto-grants-1987_11
Patent number
US04707483

Reaction notes

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