m-Chloroperbenzoic acid → 2-Chloro-6-fluoro-3-(oxiran-2-yl)benzonitrile

HRID 2175866Notes

Reaction equation

HRID 2175866 reaction equation
[Cl:1][C:2]1[C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:9]([CH:10]2[CH2:11][O:21]2)=[CH:8][CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 867270812-Chloro-6-fluoro-3-vinylbenzonitrile

Product 1

HCID 867270822-Chloro-6-fluoro-3-(oxiran-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-chloro-6-fluoro-3-vinylbenzonitrile dissolved in CHCl3 (300 mL) then added mCPBA (29.4 g, 171 mmol) and stirred at RT for 16 h. When TLC showed starting materials were consumed, the mixture was washed with Na2S2O3 (1×), 1N NaOH (1×), brine (2×), then dried over Na2SO4. Filtered and concentrated then purified by MPLC chromatography using 330 g ISCO Redi-sep column and eluted with 20% ethyl acetate/hexane solvent system to yield 2-chloro-6-fluoro-3-(oxiran-2-yl)benzonitrile.

Workup

  1. customwere consumed
  2. washthe mixture was washed with Na2S2O3 (1×), 1N NaOH (1×), brine (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationFiltered
  5. concentrationconcentrated
  6. customthen purified by MPLC chromatography
  7. washeluted with 20% ethyl acetate/hexane solvent system

Sources & evidence

ORD record
ord-4a54b361d3bf45a188b66dbf82ff6df1
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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