m-Chloroperbenzoic acid → 2,6-Difluoro-3-(oxiran-2-yl)benzonitrile

HRID 1502011Notes

Reaction equation

HRID 1502011 reaction equation
[CH:1]([C:3]1[C:4]([F: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:12][C:4]1[C:3]([CH:1]2[CH2:2][O:21]2)=[CH:10][CH:9]=[C:8]([F:11])[C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 867270603-Ethenyl-2,6-difluorobenzonitrile

Product 1

HCID 867270612,6-Difluoro-3-(oxiran-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethenyl-2,6-difluorobenzonitrile (1.70 g, 10.3 mmol) was added to DCM (10 mL) at 0° C. Then mCPBA (5.33 g, 30.9 mmol) was added and the mixture was stirred at RT for 48 h. The reaction mixture was washed with saturated aqueous Na2S2O3, then with 1N NaOH, and brine. The organic layer was separated and dried over Na2SO4, filtered, and evaporated to dryness. The crude product was purified by MPLC chromatography through a 120 g Redi-sep column, eluting with a 0-100% EtOAc/hexane solvent system. 2,6-Difluoro-3-(oxiran-2-yl)benzonitrile was isolated.

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 MPLC chromatography through a 120 g Redi-sep column
  7. washeluting with a 0-100% EtOAc/hexane solvent system

Sources & evidence

ORD record
ord-42399725c04a46878b52ec87271138fe
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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