m-Chloroperbenzoic acid → 6-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

HRID 2175813Notes

Reaction equation

HRID 2175813 reaction equation
[CH:1]([C:3]1[C:4]([CH3:12])=[C:5]([C:8]([F:11])=[CH:9][CH:10]=1)[C:6]#[N:7])=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[F:11][C:8]1[C:5]([C:6]#[N:7])=[C:4]([CH3:12])[C:3]([CH:1]2[CH2:2][O:21]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666438663-Ethenyl-6-fluoro-2-methylbenzonitrile

Product 1

HCID 866473076-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethenyl-6-fluoro-2-methylbenzonitrile (14.9 g, 92.0 mmol) was added to DCM (400 mL) at 0° C. then mCPBA (47.85 g, 277.5 mmol) was added and the mixture was stirred at RT for 72 h. The reaction mixture was washed with saturated aqueous Na2S2O3, then with 1N NaOH, and brine. The organic layer was separated, dried over Na2SO4, filtered, and evaporated to dryness. The crude product was purified by chromatography through a 330 g Redi-sep column, eluting with 0-100% hexane/DCM solvent system to afford 6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile. LC-MS: M+1=178.

Workup

  1. washThe reaction mixture was washed with saturated aqueous Na2S2O3
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by chromatography through a 330 g Redi-sep column
  7. washeluting with 0-100% hexane/DCM solvent system

Sources & evidence

ORD record
ord-32b3060df08b4f1985bc1a69d76dae06
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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