Cornforth reagent → 1-(5-Bromo-2-fluorophenyl)propan-1-one

HRID 1880375Notes

Reaction equation

HRID 1880375 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.[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]=[CH:4][C:5]([F:12])=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 589415561-(5-Bromo-2-fluorophenyl)propan-1-ol

Product 1

HCID 529838141-(5-Bromo-2-fluorophenyl)propan-1-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(5-bromo-2-fluorophenyl)propan-1-ol (12.1 g, 64.8 mmol) in CH2Cl2 (100 mL) was added pyridinium dichromate (73.2 g, 194 mmol) and powdered molecular sieves. The mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered through a pad of diatomaceous earth and washed with diethyl ether. The combined ether and CH2Cl2 layers were collected and concentrated under vacuum to afford 1-(5-bromo-2-fluorophenyl)propan-1-one (12.6 g, 98%) as a syrup. 1H NMR (CDCl3): δ 7.9-8.0 (m, 1H), 7.5-7.6 (m, 1H), 7.0 (t, 1H), 3.0-3.1 (m, 2H), 1.2 (t, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washwashed with diethyl ether
  3. customThe combined ether and CH2Cl2 layers were collected
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-548f3114d0354f64bfa93215dd4d03c8
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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