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

HRID 1640890노트

반응식

HRID 1640890 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 53%

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, 51.7 mmol) over a period of 30 min. Stir the mixture for an additional half an hour. Add iodine (9.8 g, 38.6 mmol, dissolved in 60 mL of THF). Stir for 1 h after the addition is complete. Allow the temperature to raise to RT over 1 h while stirring. Treat the mixture with water. Extract the solution with ethyl acetate three times. Wash the organic layer with aqueous saturated 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, 53%) 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 h
  2. additionafter the addition
  3. stirringwhile stirring
  4. extractionExtract the solution with ethyl acetate three times
  5. washWash the organic layer with aqueous saturated 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-40618a1aa80c4a0ca16e648ad66047d6
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114872B2

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