Cornforth reagent → 1-(4-Bromo-3-fluorophenyl)ethan-1-one

HRID 57459

Reaction equation

HRID 57459 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[F:11].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[F:11]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 717565421-(4-Bromo-3-fluorophenyl)ethan-1-ol

Product 1

HCID 228319141-(4-Bromo-3-fluorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-(4-bromo-3-fluorophenyl)ethanol oil (from Step 1) in DCM (100 mL) was added pyridinium dichromate (8.96 g, 23.82 mmol). The mixture was stirred overnight at room temperature. To the mixture was added celite, the reaction mixture was filtered through a celite pad and rinsed several times with DCM. The filtrate was concentrated under reduced pressure. The crude material was purified by column chromatography [SiO2, 40 g, heptane/ethyl acetate] providing 1-(4-bromo-3-fluorophenyl)ethanone (3.08 g) as a white solid.

Workup

  1. additionTo the mixture was added celite
  2. filtrationthe reaction mixture was filtered through a celite pad
  3. washrinsed several times with DCM
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe crude material was purified by column chromatography [SiO2, 40 g, heptane/ethyl acetate]

Sources & evidence

ORD record
ord-f098ac911451486585d6a41adb82968f
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Linked notes

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