Acetonitrile → 2-Fluoro-5-nitropyridine

HRID 367052

반응식

HRID 367052 반응식
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

참가 물질

6

반응물 3

HCID 6342AcetonitrileHCID 783082-Chloro-5-nitropyridine2회HCID 522689Potassium Fluoride

생성물 1

HCID 952642-Fluoro-5-nitropyridine수율 54%

시약·촉매·용매 2

HCID 2724163Tetraphenylphosphonium Bromide촉매HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-15c08ec3a41c4b66a02a81bb36bd2c99
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133253

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