Water → 5-Bromo-2-fluoro-3-methylbenzyl alcohol

HRID 1880432Notes

Reaction equation

HRID 1880432 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([F:10])=[C:6]([CH2:8]Br)[CH:7]=1.C(=O)(O)[O-:13].[Na+].O>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([F:10])=[C:6]([CH2:8][OH:13])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 669206545-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene

Product 1

HCID 669205355-Bromo-2-fluoro-3-methylbenzyl alcoholYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 5-bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene (6.56 g, 23.3 mmol) in acetone (150.0 mL) was added sodium bicarbonate (2.44 g, 29.1 mmol) and water (250.0 mL). The reaction was refluxed overnight. The reaction was cooled to room temperature and extracted 3× with ethyl acetate. The organic extracts were combined and washed with brine, dried over sodium sulfate and concentrated. The resultant oil was flash chromatographed (80 g silica, 5-10% ethyl acetate/hexanes gradient) to yield 2.5 g of (5-bromo-2-fluoro-3-methylphenyl)methanol as a white solid.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. extractionextracted 3× with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed (80 g silica, 5-10% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-e49c5c8413f44436b7422dac80ffc7ac
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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