Acetonitrile → 2-Fluoro-5-nitropyridine

HRID 3297

반응식

HRID 3297 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>[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

참가 물질

6

반응물 3

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

생성물 1

HCID 952642-Fluoro-5-nitropyridine

시약·촉매·용매 2

HCID 2724163Tetraphenylphosphonium Bromide촉매HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-c3b0e2987bf6463288457f21739f34ea
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733912

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