4-Bromo-2-methylbenzoic acid → (4-Bromo-2-methylphenyl)methanol

HRID 931666Notes

Reaction equation

HRID 931666 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH3:11])[CH:3]=1

Participants

3

Reactant 1

HCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanolYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-tetrahydrofuran complex (0.2 mol, 200 mL, 1.0 M solution) to a solution of 4-bromo-2-methylbenzoic acid (39 g, 0.18 mol) in tetrahydrofuran (200 mL). After 18 hours at room temperature, remove the solvent under the reduced pressure to give a solid. Purify by flash chromatography to yield the title compound as a white solid (32.9 g, 0.16 mol). 1H NMR (CDCl3): δ 1.55 (s, 1H), 2.28 (s, 3H), 4.61 (s, 2H), 7.18-7.29 (m, 3H).

Workup

  1. customremove the solvent under the reduced pressure
  2. customto give a solid
  3. customPurify by flash chromatography

Sources & evidence

ORD record
ord-c53d979a7053452693e4349a0dac5425
Source dataset
uspto-grants-2016_03
Patent number
US09296775B2

Reaction notes

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