Triethylamine → 3-Bromopyridine-2-carbonitrile

HRID 466204노트

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HRID 466204 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>C(#N)C>[C:9]([C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:11]

참가 물질

5

반응물 3

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

생성물 1

HCID 8176943-Bromopyridine-2-carbonitrile수율 26%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Under nitrogen, a solution of 156 g (0.90 mol) of 3-bromopyridine N-oxide from step 1 was dissolved in 1000 mL of acetonitrile and treated with 256 mL (1.84 mol) of triethylamine and 275 g (2.8 mol) of trimethylsilyl cyanide. The reaction was stirred at reflux overnight and concentrated in vacuo; the residue was dissolved in 2.5M aqueous sodium hydroxide and extracted with methylene chloride. The organic phase was dried (MgSO4) and concentrated in vacuo; this residue was decolorized with carbon and recrystallized from methanol to give 42.2 g (26%) of 2-cyano-3-bromopyridine as a cream colored solid: mp 97°-98° C.; NMR (CDCl3)δ7.42 (dd, J=8 and 5 Hz, 1H), 8.05 (dd, J=8 and 2 Hz, 1H), 8.67 (dd, J=5 and 2 Hz, 1H).

후처리

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue was dissolved in 2.5M aqueous sodium hydroxide
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-1249f3ca5f5a48d0b87aa88b79a3c1ec
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155117

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