m-Chloroperbenzoic acid → 2-Fluoro-4-(oxiran-2-yl)benzonitrile

HRID 1187013Notes

Reaction equation

HRID 1187013 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[F:11][C:5]1[CH:4]=[C:3]([CH:1]2[CH2:2][O:20]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 219046072-Fluoro-4-vinylbenzonitrile

Product 1

HCID 552965762-Fluoro-4-(oxiran-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-ethenyl-2-fluorobenzonitrile (18.0 g, 122 mmol) in 200 mL of DCM was slowly added mCPBA (74.8 g, 367.347 mmol) in portions at 0° C. The mixture was warmed to room temperature and stirred overnight. The solution was washed with aqueous Na2SO3 until KI paper didn't change color. The organic layers was washed with brine and then concentrated. The residue was purified via column chromatography to give 2-fluoro-4-oxiran-2-ylbenzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.59˜7.62 (m, 1H), 7.12˜7.22 (m, 2H), 3.89˜3.91 (m, 1H), 3.20˜3.22 (m, 1H), 2.72˜2.74 (m, 1H).

Workup

  1. customat 0° C
  2. washThe solution was washed with aqueous Na2SO3 until KI paper didn't change color
  3. washThe organic layers was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified via column chromatography

Sources & evidence

ORD record
ord-19b82bdc934b46819cefe92112e9dc9a
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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