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

HRID 1501987Notes

Reaction equation

HRID 1501987 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-ece37e959a7b494f8a59842fed09652b
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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