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

HRID 1187013ノート

反応式

HRID 1187013 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-19b82bdc934b46819cefe92112e9dc9a
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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