Cornforth reagent → 1-(3-Bromo-5-fluorophenyl)ethan-1-one

HRID 891953Notes

Reaction equation

HRID 891953 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:11])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[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:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 222402011-(3-broMo-5-fluorophenyl)ethanol

Product 1

HCID 137303591-(3-Bromo-5-fluorophenyl)ethan-1-oneYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-bromo-5-fluoro-phenyl)-ethanol (2.9 g, 13.2 mmol) in methylene chloride (150 ml) was added at room temperature pyridinium dichromate (3.98 g). The reaction mixture was stirred for 4 hours at room temperature and the solvent was removed in the presence of silica gel. The crude product was purified by chromatography over silica gel to provide 1-(3-bromo-5-fluoro-phenyl)-ethanone (1.39 g, 45%) as a light yellow solid, MS: m/e=216.1 (M+).

Workup

  1. customthe solvent was removed in the presence of silica gel
  2. customThe crude product was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-4822ccc0519e474595acd3da01a068ac
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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