Triethylamine → 3-Bromopyridine-2-carbonitrile

HRID 423181노트

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HRID 423181 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 8176943-Bromopyridine-2-carbonitrile수율 79%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-4abb570429de403ea86cc5008a223912
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101761B2

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