Triethylamine → 3-Bromopyridine-2-carbonitrile

HRID 466204ノート

反応式

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

参加物

5

反応物 3

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

生成物 1

HCID 8176943-Bromopyridine-2-carbonitrile収率 26%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1249f3ca5f5a48d0b87aa88b79a3c1ec
出典データセット
uspto-grants-1992_10
特許番号
US05155117

反応ノート

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