聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 5-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile

HRID 534009

反应方程式

HRID 534009 反应方程式
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[H-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.O>CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]([O:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=2)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 24758氢化钠HCID 707322,6-二甲基-3-羟基吡啶2,6-二甲基-3-羟基吡啶HCID 27696985-溴-2-氰基-3-硝基吡啶

产物 1

HCID 674864525-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile收率 101.2%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

To a 0° C. solution of 2,6-dimethylpyridin-3-ol (10 g, 81.2 mmol) in DMF (50 ml) was added sodium hydride (60% dispersion in oil, 3.4 g, 85 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (18.5 g, 81 mmol) was added and the mixture was allowed to warm slowly to ambient temperature. The reaction mixture was slowly added to 500 mL of rapidly stirring water. A light red solid formed and then the material formed a gum. The gum was extracted into ethyl acetate, and the organics washed with brine, dried over MgSO4 and concentrated in vacuo to afford 5-bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile (25 g, 82 mmol, 101% yield).

后处理

  1. customA light red solid formed
  2. customthe material formed a gum
  3. extractionThe gum was extracted into ethyl acetate
  4. washthe organics washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-d3ebc3b23e2d4d389e88503e7fd5fbc1
来源数据集
uspto-grants-2014_10
专利号
US08853409B2

关联笔记

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