Dimethylformamide → 2-(4-Bromo-2-chlorophenyl)-2-methylpropanenitrile

HRID 859721ノート

反応式

HRID 859721 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[C:6]([Cl:13])[CH:5]=1.[CH3:14]I.C[N:17]([CH:19]=O)C>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:11])[C:19]#[N:17])=[C:6]([Cl:13])[CH:5]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58762522(4-Bromo-2-chlorophenyl)acetonitrile

生成物 1

HCID 587626012-(4-Bromo-2-chlorophenyl)-2-methylpropanenitrile収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

NaH (95%, 1.18 g, 49.35 mmol) was suspended in DMF (25 mL) and cooled to 0° C. 4-bromo-2-chloro-phenyl)-acetonitrile (2.27 g, 9.87 mmol) from step 3 above, was dissolved in THF (10 mL) and slowly added via cannula and the reaction mixture stirred 20 min. MeI (6.10 mL, 98 mmol) was added and the resulting mixture was stirred overnight at room temperature. Reaction was quenched with H2O (50 mL). Solvents were removed in vacuo and residue partitioned between EtOAc and 1N HCl (50 mL). The organic phase was dried over Na2SO4 and evaporated. The crude organic product was purified by flash column chromatography (5% EtOAc in hexanes) to give the product (2.23 g, 87%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.34 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 2.0 Hz, 1H), 7.61 (d, J=1.8 Hz, 1H).

後処理

  1. additionslowly added via cannula
  2. stirringthe resulting mixture was stirred overnight at room temperature
  3. customReaction
  4. customwas quenched with H2O (50 mL)
  5. customSolvents were removed in vacuo and residue
  6. custompartitioned between EtOAc and 1N HCl (50 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customevaporated
  9. customThe crude organic product was purified by flash column chromatography (5% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-7616858575024105b8e4ef93f6e2d091
出典データセット
uspto-grants-2006_12
特許番号
US07151105B2

反応ノート

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