Water → 3-Bromo-2,6-difluorophenol

HRID 1455489Notes

Reaction equation

HRID 1455489 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>C1COCC1>[OH:22][C:15]1[C:10]([F:9])=[C:11]([Br:17])[CH:12]=[CH:13][C:14]=1[F:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 676741-Bromo-2,4-difluorobenzeneHCID 45051747Lithium diisopropylamine

Product 1

HCID 183711103-Bromo-2,6-difluorophenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

A quantity of 40.2 ml of 2.0 M lithium diisopropylamine (LDA) is dissolved in 80 ml of THF 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 to 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 to 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-367614ae779b4cbab938412c374702a3
Source dataset
uspto-grants-2009_01
Patent number
US07482454B2

Reaction notes

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