Acetonitrile → 2-Fluoro-5-nitropyridine

HRID 3297

反応式

HRID 3297 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F-:11].[K+].C(#N)C>[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br-].CCOCC>[F:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 6342AcetonitrileHCID 783082-Chloro-5-nitropyridineHCID 522689Potassium Fluoride

生成物 1

HCID 952642-Fluoro-5-nitropyridine

試薬・触媒・溶媒 2

HCID 2724163Tetraphenylphosphonium Bromide触媒HCID 3283Diethyl Ether溶媒

実験手順

2-Chloro-5-nitropyridine (100 g, 0.656 mol, Aldrich), KF (84.1 g, 1.448 mol), Ph4PBr (95.3 g, 0.227 mol) and acetonitrile (1.5 L) were combined and heated at reflux until no starting material remained. The volume was reduced to 750 mL, and the mixture was diluted with 2 L of ether, filtered and concentrated. The residue was triturated with hot hexane (5×1 L). The hexane extracts were combined and concentrated to afford 48 g (54%). 1H NMR (CDCl3, 300 MHz) δ7.15 (dd, J=3, 6 Hz, 1H), 8.64 (m, 1H), 9.15 (d, J=1.6 Hz, 1H).

後処理

  1. temperatureheated
  2. temperatureat reflux until no starting material
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with hot hexane (5×1 L)
  6. concentrationconcentrated
  7. customto afford 48 g (54%)

出典と根拠

ORDレコード
ord-c3b0e2987bf6463288457f21739f34ea
出典データセット
uspto-grants-1998_03
特許番号
US05733912

関連ノート

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