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

HRID 1502050Notes

Reaction equation

HRID 1502050 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-d6fa682fd5e148d68f66fc84d80834ae
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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