Acetonitrile → 2-Fluoro-5-nitropyridine

HRID 367052

反応式

HRID 367052 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>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.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-nitropyridine2 回HCID 522689Potassium Fluoride

生成物 1

HCID 952642-Fluoro-5-nitropyridine収率 54%

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), potassium fluoride (84.1 g, 1.45 mol, Aldrich), tetraphenylphosphonium bromide (95.3 g, 0.227 mol, Aldrich), and acetonitrile (1.5 L) were combined and heated at reflux until consumption of the 2-chloro-5-nitropyridine was complete. The volume of the mixture was reduced to 750 mL, diluted with 2 L of ether, filtered and concentrated. The resultant residue was triturated with hot hexane, and the combined hexane extracts were concentrated to give of the title compound (48 g, 54%): 1H NMR (CDCl3, 300 MHz) δ 7.15 (dd, J=3, 6 Hz, 1H), 8.64 (m, 1H), 9.15 (d, J=1.6 Hz, 1H).

後処理

  1. temperatureheated
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe resultant residue was triturated with hot hexane
  5. concentrationthe combined hexane extracts were concentrated

出典と根拠

ORDレコード
ord-15c08ec3a41c4b66a02a81bb36bd2c99
出典データセット
uspto-grants-2000_10
特許番号
US06133253

関連ノート

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