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

HRID 1187013노트

반응식

HRID 1187013 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-19b82bdc934b46819cefe92112e9dc9a
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673920B2

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