Cornforth reagent → 1-(5-Bromo-2-fluoropyridin-3-yl)ethan-1-one

HRID 627646Notes

Reaction equation

HRID 627646 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Br:22][C:23]1[CH:24]=[C:25]([CH:30]([OH:32])[CH3:31])[C:26]([F:29])=[N:27][CH:28]=1>C(Cl)Cl>[Br:22][C:23]1[CH:24]=[C:25]([C:30](=[O:32])[CH3:31])[C:26]([F:29])=[N:27][CH:28]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 426090481-(5-Bromo-2-fluoropyridin-3-yl)ethan-1-ol

Product 1

HCID 401519061-(5-Bromo-2-fluoropyridin-3-yl)ethan-1-oneYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyridinium dichromate (55.4 g, 147 mmol) in DCM (100 mL) was brought to 0° C. and a solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanol (10.8 g, 49.1 mmol) in DCM (30 mL) was added. The reaction was allowed to warmed to room temperature and stirred for 48 h. The mixture was filtered through Celite, washed with DCM and concentrated to afford 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (11 g, 51 mmol, 100% yield) as a light yellow solid. LC/MS (ESI+) m/z=218 (M+H).

Workup

  1. customwas brought to 0° C.
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with DCM
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5f650fbe76bb4737be2a1a859f0c582b
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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