Sodium Cyanide → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 7698

反応式

HRID 7698 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.[C-:11]#[N:12].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:11]#[N:12])=[C:4]([F:10])[CH:3]=1

参加物

4

反応物 2

HCID 8929Sodium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

生成物 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 17 mmol). The reaction mixture was stirred at 90° C. for 1 h, cooled to rt and quenched with brine (50 mL). After extraction with EtOAc (3×100 mL), the organic layers were combined, washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1) to afford 4-bromo-2-fluoro benzyl cyanide as yellow solid. MS (ESI) 307 (M+H)+.

後処理

  1. temperaturecooled to rt
  2. customquenched with brine (50 mL)
  3. extractionAfter extraction with EtOAc (3×100 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1)

出典と根拠

ORDレコード
ord-bdc28b5ce6e24691832732f0a37423ba
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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