Pyridine → 2-Chloro-6-fluoro-3-(2-oxoethyl)benzonitrile

HRID 2173219Notes

Reaction equation

HRID 2173219 reaction equation
[Cl:1][C:2]1[C:9]([CH2:10][CH:11]=C)=[CH:8][CH:7]=[C:6]([F:13])[C:3]=1[C:4]#[N:5].N1C=CC=CC=1.[O:20]=[O+][O-]>C(Cl)Cl.CO>[Cl:1][C:2]1[C:9]([CH2:10][CH:11]=[O:20])=[CH:8][CH:7]=[C:6]([F:13])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24823OzoneHCID 675161222-Chloro-6-fluoro-3-(prop-2-en-1-yl)benzonitrile

Product 1

HCID 866930062-Chloro-6-fluoro-3-(2-oxoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-chloro-6-fluoro-3-(prop-2-en-1-yl)benzonitrile (450 mg, 2.296 mmol) in 0.37 mL pyridine (363 mg, 4.592 mmol) and 40 mL DCM/MeOH (V/V=1:1) was bubbled O3 at −78° C. for 15 min. Then N2 was bubbled for another 15 min. at −78° C. and 5 mL of Me2S were added. The mixture was stirred at r.t. overnight and then concentrated to dryness. The residue was dissolve in EtOAc (50 mL) and washed with 1 N HCl (aq.) and brine, dried over anhydrous Na2SO4 and concentrated to dryness to give 2-chloro-6-fluoro-3-(2-oxoethyl)benzonitrile.

Workup

  1. customThen N2 was bubbled for another 15 min. at −78° C.
  2. addition5 mL of Me2S were added
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolve in EtOAc (50 mL)
  5. washwashed with 1 N HCl (aq.) and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b9611788c5d5445eb05d1474b1476c32
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…