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

HRID 537026

反応式

HRID 537026 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 102432202-Fluoro-3-iodo-5-methylpyridine収率 499.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-16a6e59ce02b4fb3b5c3aec2a9000e59
出典データセット
uspto-grants-2014_10
特許番号
US08859768B2

関連ノート

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