3-bromo-2,4-dimethylbenzoic acid → 3-Bromo-2,4-dimethylbenzenemethanol

HRID 1474194Notes

Reaction equation

HRID 1474194 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

3

Reactant 1

HCID 224422683-bromo-2,4-dimethylbenzoic acid

Product 1

HCID 666439253-Bromo-2,4-dimethylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-2,4-dimethylbenzoic acid (6.50 g, 28.4 mmol), in THF (50 mL) was treated with borane tetrahydrofuran complex (42.6 mL, 42.6 mmol) and stirred for 12 h. Analysis by LC indicated that reaction had gone to completion. The solution was concentrated to dryness, redissolved in DCM, and washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The resulting (3-bromo-2,4-dimethylphenyl)methanol was used for the next step with out further purification. 1H-NMR (CDCl3, 500 MHz), δ 7.227 (d, J=7.5 Hz, 1H), 7.122 (d, J=7.5 Hz, 1H), 4.730 (m, 2H), 2.492 (s, 3H), 2.456 (s, 3H).

Workup

  1. customAnalysis by LC indicated that reaction
  2. concentrationThe solution was concentrated to dryness
  3. dissolutionredissolved in DCM
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting (3-bromo-2,4-dimethylphenyl)methanol was used for the next step with out further purification

Sources & evidence

ORD record
ord-f43dc84ad0db48ddae326ef8969cd7c6
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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