Bromhydrol → (+)-3-Fluoro 4-(2-methyloctanoyl) phenol

HRID 2372252Notes

Reaction equation

HRID 2372252 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:18]C)[CH:5]=[CH:6][C:7]=1[C:8](=[O:17])[CH:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[Br-].[Al+3].[Br-].[Br-]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([OH:18])[CH:5]=[CH:6][C:7]=1[C:8](=[O:17])[CH:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 15027240(+)-3-Fluoro-4-(2-methyloctanoyl) anisole

Product 1

HCID 15027241(+)-3-Fluoro 4-(2-methyloctanoyl) phenolYield 101.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Then, 0.57 g (2.14 mmol) of the above (+)-3-fluoro-4-(2-methyloctanoyl) anisole and 6 ml of dried toluene were placed in a flask, to which was added 1.78 g (6.67 mmol) of anhydrous aluminum bromide while cooling on ice water. The resulting mixture was stirred under the cooling on ice water for 30 minutes and at room temperature for 6.5 hours. The reaction mixture was poured into 30 ml of ice water and extracted with toluene. The organic layer was washed with water, dried on magnesium sulfate, filtered and concentrated to obtain 0.55 g (2.18 mmol, yield: 100%) of brown oily 3-fluoro-4-(2-methyloctanoyl) phenol having the aforementioned physical and chemical properties.

Workup

  1. temperaturewhile cooling on ice water
  2. waitat room temperature for 6.5 hours
  3. extractionextracted with toluene
  4. washThe organic layer was washed with water
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fddee806174e435e8b26e39f8d2773d2
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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