2-氯-3-甲基-5-硝基吡啶 → 2-氟-3-甲基-5-硝基吡啶

HRID 3315

反应方程式

HRID 3315 反应方程式
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

参与物

6

反应物 2

HCID 896482-氯-3-甲基-5-硝基吡啶HCID 522689氟化钾

产物 1

HCID 124081842-氟-3-甲基-5-硝基吡啶收率 61.9%

试剂、催化剂与溶剂 3

HCID 2724163四苯基溴化膦催化剂HCID 3283乙醚溶剂HCID 6342乙腈溶剂

实验过程

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)+.

后处理

  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

来源与证据

ORD记录
ord-2530436b50534fbdbbf72c2ea6ad27e3
来源数据集
uspto-grants-1998_03
专利号
US05733912

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