4-(Bromomethyl)benzoic acid → 4-(Bromomethyl)benzyl alcohol

HRID 5926

Reaction equation

HRID 5926 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.B.C1COCC1>C1COCC1>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 225994-(Bromomethyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 103304344-(Bromomethyl)benzyl alcoholYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-bromomethylbenzoic acid (5.04; 23.3 mmol) in THF (30 ml) was cooled to 0° C. and treated with borane/THF (35 mmol). The ice bath was removed and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The excess borane was quenched with MeOH, and then with water, and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 4% HCl, water NaHCO3, brine, dried (MgSO4), filtered, concentrated in vacuo to afford 4.44 g (94%) of the title compound.

Workup

  1. customThe ice bath was removed
  2. temperatureto warm to room temperature
  3. customThe excess borane was quenched with MeOH
  4. concentrationwith water, and the reaction mixture was concentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 4% HCl, water NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64a0c4283173496db827ea2c2506a2c6
Source dataset
uspto-grants-1993_09
Patent number
US05246944

Linked notes

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