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

HRID 1640890ノート

反応式

HRID 1640890 の反応式
[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

参加物

6

反応物 4

HCID 807IodineHCID 962WaterHCID 66738421HCID 66738421、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 667381532-Fluoro-4-iodo-5-(methoxymethoxy)pyridine収率 53%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-40618a1aa80c4a0ca16e648ad66047d6
出典データセット
uspto-grants-2012_02
特許番号
US08114872B2

反応ノート

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