Hydrogen Peroxide → 2-Chloro-3-fluorophenol

HRID 1043105Notes

Reaction equation

HRID 1043105 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-4ce71c42f03741008358fcab2495bdc7
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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