Potassium Cyanide → 2-(4-Bromo-3-fluorophenyl)acetonitrile

HRID 1050046ノート

反応式

HRID 1050046 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][C:3]=1[F:10].[C-:11]#[N:12].[K+]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:11]#[N:12])=[CH:4][C:3]=1[F:10]

参加物

4

反応物 2

HCID 9032Potassium CyanideHCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzene

生成物 1

HCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrile収率 79.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 1-bromo-4-(bromomethyl)-2-fluorobenzene (1 g, 3.73 mmol) in EtOH (30 mL) was added KCN (0.243 g, 3.73 mmol). The resulting mixture was stirred at 60° C. After 3 h, LCMS analysis showed the starting material had disappeared. The solvent was removed in vacuo. The residue was dissolved in EA (80 mL) was washed with H2O (30 mL) and brine (30 mL). The organic layer was dried and concentrated to give the crude product, which was purified by silica column chromatography (PE/EA=10/1) to yield a white solid of 2-(4-bromo-3-fluorophenyl)acetonitrile (0.78 g, 2.96 mmol, 79.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.63 (t, J=7.8 Hz, 1H), 7.24 (d, J=9.2 Hz, 1H), 7.12 (d, J=9.6 Hz, 1H), 3.92 (s, 2H); ES-LCMS m/z 214.0 (M+H).

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in EA (80 mL)
  3. washwas washed with H2O (30 mL) and brine (30 mL)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by silica column chromatography (PE/EA=10/1)

出典と根拠

ORDレコード
ord-2bcbb15271334ff899a5b77fce2ea0cf
出典データセット
uspto-grants-2016_07
特許番号
US09382238B2

反応ノート

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