Iodine → 2-Fluoro-4-iodo-5-(methoxymethoxy)pyridine

HRID 561002노트

반응식

HRID 561002 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][N:3]=1.C([Li])(C)(C)C.[I:17]I.O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([I:17])[C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 962WaterHCID 66738421HCID 66738421, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 667381532-Fluoro-4-iodo-5-(methoxymethoxy)pyridine수율 52.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Cool a solution of 2-fluoro-5-methoxymethoxy-pyridine (4.1 g, 26.1 mmol) in THF (60 mL) to −75° C. Add tert-butyllithium (1.7 M in pentane, 30.4 mL, 51.66 mmol) over a period of 30 min. Stir the mixture for an additional half an hour. Add iodine (9.8 g, 38.61 mmol, dissolved in 60 mL of tetrahydrofuran). Stir for 1 hour after the addition is complete. Allow the temperature to rise to room temperature over 1 hour while stirring. Treat the mixture with water. Extract the solution with ethyl acetate three times. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown solid. Triturate the brown solid with hexane. Filter to afford the title compound (3.9 g, 52.8%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 3.53 (s, 3H), 5.23 (s, 2H), 7.39 (d, J=4.0 Hz, 1H), 7.96 (d, J=1.6 Hz, 1H).

후처리

  1. stirringStir for 1 hour
  2. additionafter the addition
  3. stirringwhile stirring
  4. extractionExtract the solution with ethyl acetate three times
  5. washWash the organic layer with saturated aqueous sodium chloride
  6. dry with materialDry the mixture over sodium sulfate
  7. concentrationConcentrate the solution in vacuo to a brown solid
  8. customTriturate the brown solid with hexane
  9. filtrationFilter

출처 및 근거

ORD 기록
ord-16eb4cb0de8348eebf7ab232e05246d4
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063212B2

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