Pyridine → 2-Fluoro-4-(2-oxoethyl)benzonitrile

HRID 1519628Notes

Reaction equation

HRID 1519628 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([F:12])[CH:5]=1)[CH:2]=C.N1C=CC=CC=1.[O:19]=[O+][O-]>C(Cl)Cl.CO>[F:12][C:6]1[CH:5]=[C:4]([CH2:1][CH:2]=[O:19])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24823OzoneHCID 247217663-(4-Cyano-3-fluorophenyl)-1-propene

Product 1

HCID 866944782-Fluoro-4-(2-oxoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-allyl-2-fluorobenzonitrile (1 g, 6.2 mmol) in 1:1 CH2Cl2/MeOH (40 mL) containing pyridine (1 mL, 12.4 mmol) was cooled to −78° C., and O3 was passed through until a blue color was present. N2 was then bubbled through to discharge the blue color and Me2S (5 ml) was added. The reaction mixture was allowed to warm and left overnight. The mixture was washed with 1 N HCl and aqueous NaHCO3 and then dried and concentrated to give crude 2-fluoro-4-(2-oxoethyl)benzonitrile. The material was carried on as the crude.

Workup

  1. customN2 was then bubbled through
  2. additionwas added
  3. temperatureto warm
  4. washThe mixture was washed with 1 N HCl and aqueous NaHCO3
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-289332fe76a04211aa8fe099e7eb83e7
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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