Potassium Carbonate → (4-Bromo-2-methylphenyl)methanol

HRID 2189432Notes

Reaction equation

HRID 2189432 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.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanolYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-methylbenzoic acid (10 g) in tetrahydrofuran (60 mL) was added borane-dimethylsulfide complex (7.07 g) under ice-cooling. The reaction mixture was stirred at room temperature for 5 minutes, and stirred at 75° C. for 2 days. The reaction mixture was cooled to room temperature. A saturated aqueous potassium carbonate solution was added to the reaction mixture, and the organic layer was separated. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (9.0 g).

Workup

  1. temperaturecooling
  2. stirringstirred at 75° C. for 2 days
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe organic layer was separated
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-af0803f987ab42fd8bf59e14d0f9f577
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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