Iodine → 2-Fluoro-3-iodo-5-methylpyridine

HRID 537026

반응식

HRID 537026 반응식
[Li+].CC([N-]C(C)C)C.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1.[I:17]I>C1COCC1.O>[F:9][C:10]1[C:15]([I:17])=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1

참가 물질

6

반응물 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 27746352-Fluoro-5-methylpyridine

생성물 1

HCID 102432202-Fluoro-3-iodo-5-methylpyridine수율 499.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매4회

반응 조건

온도
-78 °C

실험 절차

A solution of 2M LDA in THF (371 mL, 742 mmol) was added to THF (1400 mL) at −78° C. under an atmosphere of nitrogen. To this stirred, cooled solution was added 2-fluoro-5-methylpyridine (75.0 g, 67.6 mmol) in THF (280 mL) dropwise. The reaction mixture was allowed to stir at −78° C. for 2 h and then a solution of iodine (171.5 g, 67.6 mmol) in THF (560 mL) was added dropwise. The reaction mixture was allowed to stir at −78 for 2 h and then diluted with water (875 mL). The mixture was allowed to warm to rt and was then extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-fluoro-3-iodo-5-methylpyridine (80 g, 50%).

후처리

  1. temperatureTo this stirred, cooled solution
  2. stirringto stir at −78 for 2 h
  3. temperatureto warm to rt
  4. extractionwas then extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-16a6e59ce02b4fb3b5c3aec2a9000e59
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859768B2

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