Hydrogen Peroxide → 3-Bromo-2-fluorophenol

HRID 1018403Notes

Reaction equation

HRID 1018403 reaction equation
[OH:1]O.[Br:3][CH:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1(B(O)O)[F:10].O>COC(C)(C)C>[Br:3][C:4]1[C:5]([F:10])=[C:6]([OH:1])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 70153732HCID 70153732, compound

Product 1

HCID 184012573-Bromo-2-fluorophenol

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

125 ml of a 35% strength aqueous solution of hydrogen peroxide are added dropwise at room temperature to the crude 2-bromo-1-fluorophenylboronic acid (80 g) dissolved in 300 ml of tert-butyl methyl ether; during this addition, the temperature rises to 55° C. When the addition is complete, the mixture is refluxed for a further 2 hours. After the mixture has been cooled, 100 ml of water are added, and the organic phase is extracted by shaking twice with saturated sodium sulfite solution. After the solvent has been removed by distillation under reduced pressure, vacuum distillation (90° C.; 4 mbar) gives 54 g of 3-bromo-2-fluorophenol as an oil which soon crystallizes. 1H-NMR (CDCl3): 6.9-7.1 (m; 3H); 5.1 (br; 1H), 19F-NMR (CDCl3): −135 ppm.

Workup

  1. additionduring this addition
  2. customrises to 55° C
  3. additionWhen the addition
  4. temperaturethe mixture is refluxed for a further 2 hours
  5. temperatureAfter the mixture has been cooled
  6. extractionthe organic phase is extracted
  7. customAfter the solvent has been removed by distillation under reduced pressure, vacuum distillation (90° C.; 4 mbar)

Sources & evidence

ORD record
ord-067336817f0e452aaadd800fce1b27f8
Source dataset
uspto-grants-2002_11
Patent number
US06482478B1

Reaction notes

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