tert-Butyl hydroperoxide → 3-Bromo-2,6-difluorophenol

HRID 1699999Notes

Reaction equation

HRID 1699999 reaction equation
C(NC(C)C)(C)C.[Li].[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[Br:17].C([O:22]O)(C)(C)C>O>[OH:22][C:15]1[C:10]([F:9])=[C:11]([Br:17])[CH:12]=[CH:13][C:14]=1[F:16]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 676741-Bromo-2,4-difluorobenzeneHCID 45051747Lithium diisopropylamine

Product 1

HCID 183711103-Bromo-2,6-difluorophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-65 °C

Procedure

A quantity of 40.2 ml of 2.0 M lithium diisopropylamine (LDA) is dissolved in 80 ml of TIF at −78° C. and 15.4 g of 2,4-difluorobromobenzene is added keeping the temperature below −65° C. The reaction is stirred at −65° C. for 2 hours and 6.6 ml of 6 M anhydrous t-butyl hydroperoxide is added. After warming at room temperature, 100 ml of water is added and the mixture acidified. The solvent is removed by evaporation and the aqueous layer extracted with ether. The extracts are dried and then concentrated to give the desired product.

Workup

  1. customthe temperature below −65° C
  2. temperatureAfter warming at room temperature
  3. customThe solvent is removed by evaporation
  4. extractionthe aqueous layer extracted with ether
  5. customThe extracts are dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05f23cd9ca384db8a6cc9d57fab95e68
Source dataset
uspto-grants-2002_02
Patent number
US06348624B1

Reaction notes

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