2-Chloro-3-methyl-5-nitropyridine → 2-Fluoro-3-methyl-5-nitropyridine

HRID 3315

反応式

HRID 3315 の反応式
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[F-:12].[K+]>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C.CCOCC>[F:12][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

参加物

6

反応物 2

HCID 896482-Chloro-3-methyl-5-nitropyridineHCID 522689Potassium Fluoride

生成物 1

HCID 124081842-Fluoro-3-methyl-5-nitropyridine収率 61.9%

試薬・触媒・溶媒 3

HCID 2724163Tetraphenylphosphonium Bromide触媒HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

2-Chloro-3-methyl-5-nitropyridine (15 g, 86.9 mmol; from Maybridge Chemical Co.), KF (12 g, 258 mmol) and tetraphenylphosphonium bromide (20 g, 47.7 mmol; Aldrich) were combined in 200 mL of acetonitrile and heated at reflux for 4 days. The mixture was diluted with Et2O (500 mL) and filtered, and the filtrate was concentrated. The residue was triturated with hot hexane (4×200 mL), and the hexane solutions were combined and concentrated to afford the title compound as a solid (8.4 g, 60%): 1H NMR (DMSO-d6, 300 MHz) δ2.42 (s, 3H), 8.43 (m, 1H), 8.95 (dd, J=1.6 Hz, 1H); MS (CI/NH3) m/z: 157 (M+H)+.

後処理

  1. temperatureheated
  2. temperatureat reflux for 4 days
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was triturated with hot hexane (4×200 mL)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-2530436b50534fbdbbf72c2ea6ad27e3
出典データセット
uspto-grants-1998_03
特許番号
US05733912

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