Triethylamine → 3-Bromopyridine-2-carbonitrile

HRID 423181ノート

反応式

HRID 423181 の反応式
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([N:11](CC)CC)C.C[Si](C#N)(C)C.[OH-].[Na+]>C(#N)C>[Br:1][C:2]1[C:3]([C:9]#[N:11])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 142763Pyridine, 3-bromo-, 1-oxide

生成物 1

HCID 8176943-Bromopyridine-2-carbonitrile収率 79%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

3-Bromo-pyridine 1-oxide (9.4 g, 54 mmol) is dissolved in acetonitrile (60 mL) and triethylamine (15 mL) is added followed by trimethylsilyl cyanide (21.7 mL, 163 mmol). The mixture is heated to 100° C. and stirred for 16 h. The mixture is cooled to 0° C., poured into 250 mL of 5 M aqueous NaOH, and extracted with dichloromethane. The combined extracts are washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified using flash chromatography (Biotage® Si65M, 20% AcOEt/hexane) yields 7.8 g (79%) of the title compound as a yellow solid. GCMS m/e 182 [M−H]−.

後処理

  1. temperatureThe mixture is cooled to 0° C.
  2. extractionextracted with dichloromethane
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material is purified

出典と根拠

ORDレコード
ord-4abb570429de403ea86cc5008a223912
出典データセット
uspto-grants-2012_01
特許番号
US08101761B2

反応ノート

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