Pyridine → HCID 86694483, compound

HRID 1519638Notes

Reaction equation

HRID 1519638 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:12][CH:13]([F:15])[F:14])[CH:5]=1)[CH:2]=C.N1C=CC=CC=1.[O:22]=[O+][O-]>C(Cl)Cl.CO>[F:14][CH:13]([F:15])[O:12][C:6]1[CH:5]=[C:4]([CH2:1][CH:2]=[O:22])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24823OzoneHCID 67513193HCID 67513193, compound

Product 1

HCID 86694483HCID 86694483, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-allyl-2-(difluoromethoxy)benzonitrile (600 mg, 2.9 mmol) in 1:1 CH2Cl2/MeOH (15 mL) containing pyridine (0.5 mL, 6 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, aqueous NaHCO3, dried and concentrated to give crude 2-(difluoromethoxy)-4-(2-oxoethyl)benzonitrile.

Workup

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

Sources & evidence

ORD record
ord-6b9fb73dc52842eeaac7b46cdc55eff2
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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