Hydrogen Peroxide → 2-Chloro-3-fluorophenol

HRID 1848852Notes

Reaction equation

HRID 1848852 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[OH:12]O>O1CCCC1.[OH-].[Na+]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:12]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 22309459(2-Chloro-3-fluorophenyl)boronic acid

Product 1

HCID 112058402-Chloro-3-fluorophenol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-chloro-3-fluorophenylboronic acid (5.0 g) in tetrahydrofuran (50 mL) and 1M aqueous NaOH (30 mL) at 0° C. was added 30% hydrogen peroxide solution (4 mL), and the reaction was stirred for 2 hours. The reaction was quenched with saturated aqueous Na2S2O3 solution, acidified with concentrated aqueous HCl, and extracted twice with ethyl acetate. The combined extracts were washed with brine, concentrated, and chromatographed on silica gel using 10% ethyl acetate/hexanes as eluent to give the product.

Workup

  1. customThe reaction was quenched with saturated aqueous Na2S2O3 solution
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. concentrationconcentrated
  5. customchromatographed on silica gel using 10% ethyl acetate/hexanes as eluent
  6. customto give the product

Sources & evidence

ORD record
ord-bdc5045d6a0e47269e68a87a2599f52e
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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