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

HRID 1186936Notes

Reaction equation

HRID 1186936 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-e88e5761637c4e3287a7f2d208498d4b
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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