4-Bromo-3-methylbenzoic acid → (4-Bromo-3-methylphenyl)methanol

HRID 1662308Notes

Reaction equation

HRID 1662308 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH3:11]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH3:11]

Participants

3

Reactant 1

HCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-3-methylbenzoic acid (available from Aldrich) (4.0 g, 18.6 mmol) in THF (20 mL) was treated with borane THF complex (27.9 mL, 27.9 mmol) and allowed to stir overnight at room temperature. The reaction mixture was quenched with MeOH, diluted with EtOAc, washed with water, brine, the organics dried over Na2SO4 and concentrated. The crude was purified by combiflash (0 to 40% EtOAc/hexane) yielding 1.1 (3.09 g, 82.6% yield).

Workup

  1. customThe reaction mixture was quenched with MeOH
  2. additiondiluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialthe organics dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude was purified by combiflash (0 to 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-89b0f4284f464cfc925d9bac4fc74e2f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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