Water → 2-(4-Bromo-2-methylphenyl)acetonitrile

HRID 419961ノート

反応式

HRID 419961 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([CH3:10])[CH:3]=1.[C-:11]#[N:12].[Na+].O.C([O-])(O)=O.[Na+]>CN(C=O)C.CCCCCC.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:11]#[N:12])=[C:4]([CH3:10])[CH:3]=1

参加物

7

反応物 4

HCID 962Water2 回HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzene

生成物 1

HCID 184142962-(4-Bromo-2-methylphenyl)acetonitrile収率 93%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21584099Diethylether hexane溶媒

反応条件

温度
2.5 °C

実験手順

1-Bromo-4-(bromomethyl)-3-methylbenzene (13.2 g, 50.1 mmol) is dissolved in DMF (65 mL). The reaction mixture is cooled to 0-5° C. and NaCN (3.66 g, 74.6 mmol) is added follow by water (8 mL). The reaction is stirred overnight at room temperature and water (170 mL) is added followed by NaHCO3 sat. (130 mL) and hexane/Et2O (2:1) (150 mL). The organic phase is separated and the aqueous phase extracted with hexane/Et2O (2:1) (3×150 mL). The combined organic phases are washed with water (170 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide the expected product 2-(4-bromo-2-methylphenyl)acetonitrile (9.76 g, 93%) as an orange oil. 1H NMR (300 MHz, CHLOROFORM-D): δ 7.40-7.32 (2H, m), 7.23 (2H, d, J=8.2 Hz), 3.61 (2H, s), 2.32 (3H, s).

後処理

  1. customThe organic phase is separated
  2. extractionthe aqueous phase extracted with hexane/Et2O (2:1) (3×150 mL)
  3. washThe combined organic phases are washed with water (170 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-70edee8f859e4327af6096fdf225829a
出典データセット
uspto-grants-2012_01
特許番号
US08093402B2

反応ノート

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