Alumina → 1-(5-Bromo-2-fluorophenyl)propan-1-one

HRID 408534Notes

Reaction equation

HRID 408534 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH:8]([OH:11])[CH2:9][CH3:10])[CH:7]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 9989226AluminaHCID 589415561-(5-Bromo-2-fluorophenyl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 529838141-(5-Bromo-2-fluorophenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10 g (42.9 mmol) 1-(5-bromo-2-fluorophenyl)-1-propanol (Example 3A), 8.75 g (85.8 mmol) neutral aluminium oxide and 18.5 g (85.8 mmol) pyridinium chlorochromate in dichloromethane (100 ml) was stirred at room temperature for 4 h. The mixture was then filtered through silica gel (200 g, 0.06-0.2 mm) which was thoroughly washed with dichloromethane (1000 ml). The combined filtrates were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude title compound thus obtained (8.6 g, 87% of th.) was used in the next step without further purification.

Workup

  1. filtrationThe mixture was then filtered through silica gel (200 g, 0.06-0.2 mm) which
  2. washwas thoroughly washed with dichloromethane (1000 ml)
  3. washThe combined filtrates were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94158c9357d74f67a4c107f7b82b5772
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

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