m-Chloroperbenzoic acid → HCID 86727070, compound

HRID 1502020Notes

Reaction equation

HRID 1502020 reaction equation
[CH:1]([C:3]1[C:4]([O:12][CH3:13])=[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:22])C=1>C(Cl)Cl>[F:11][C:8]1[C:5]([C:6]#[N:7])=[C:4]([O:12][CH3:13])[C:3]([CH:1]2[CH2:2][O:22]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86727069HCID 86727069, compound

Product 1

HCID 86727070HCID 86727070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethenyl-6-fluoro-2-methoxybenzonitrile (1.67 g, 9.43 mmol) was added to DCM (50 mL) at 0° C. then mCPBA (4.88 g, 28.3 mmol) was added and the reaction mixture was stirred at RT for 16 h. The reaction mixture was washed with saturated aqueous Na2S2O3, then with 1N NaOH followed by brine. The organic layer was separated and dried over Na2SO4, filtered, and evaporated to dryness. The crude product was purified by chromatography through a 120 g. Redi-sep column and eluting with a 0-100% EtOAc/hexane solvent system. Isolated pure 6-fluoro-2-methoxy-3-(oxiran-2-yl)benzonitrile.

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 120 g
  7. washRedi-sep column and eluting with a 0-100% EtOAc/hexane solvent system

Sources & evidence

ORD record
ord-53b9ea3f005c4404a7c96e6f0041d116
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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