Pyridine → 3-Acetyl-4-fluorobenzonitrile

HRID 398358Notes

Reaction equation

HRID 398358 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[CH:16]([OH:18])[CH3:17]>C(Cl)Cl.CCOCC.[O-2].[O-2].[O-2].[Cr+6]>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([F:7])=[C:9]([C:16](=[O:18])[CH3:17])[CH:10]=1)#[N:13]

Participants

6

Reactant 2

HCID 1049PyridineHCID 230001664-Fluoro-3-(1-hydroxyethyl)benzonitrile

Product 1

HCID 230002093-Acetyl-4-fluorobenzonitrile

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridine (3.52 mL, 43.6 mmol) in CH2Cl2 (10 mL) was added dry chromium trioxide (2.18 g, 21.80 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 30 min. 4-fluoro-3-(1-hydroxyethyl)benzonitrile (600 mg, 3.63 mmol) dissolved in CH2Cl2 (10 mL) was added via canula. The reaction mixture was stirred for 10 min. and was diluted with ether and celite and stirred for an additional 20 min. The reaction mixture was filtered through a pad of celite and washed with ethyl acetate. The organic was washed then with 5% HCl and sat'd NaHCO3, brine, dried over MgSO4, and concentrated in vacuo to provide product:

Workup

  1. additionwas added via canula
  2. stirringThe reaction mixture was stirred for 10 min.
  3. stirringstirred for an additional 20 min
  4. filtrationThe reaction mixture was filtered through a pad of celite
  5. washwashed with ethyl acetate
  6. washThe organic was washed
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto provide product

Sources & evidence

ORD record
ord-038e7fabcbb3469f8fbe081927318655
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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