Iodine → 5-Chloro-3-fluoro-4-iodopicolinonitrile

HRID 2262686ノート

反応式

HRID 2262686 の反応式
[Li+].CC([N-]C(C)C)C.[Cl:9][C:10]1[CH:11]=[C:12]([F:18])[C:13]([C:16]#[N:17])=[N:14][CH:15]=1.[I:19]I>C1COCC1>[Cl:9][C:10]1[C:11]([I:19])=[C:12]([F:18])[C:13]([C:16]#[N:17])=[N:14][CH:15]=1

参加物

5

反応物 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 220135625-Chloro-3-fluoropyridine-2-carbonitrile

生成物 1

HCID 595945425-Chloro-3-fluoro-4-iodopicolinonitrile収率 82.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a cooled (−78° C.) solution of LDA (34.9 mmol, 1.1 equiv) in dry THF (200 mL) was added dropwise 5-chloro-3-fluoropicolinonitrile (5 g, 31.9 mmol) in dry THF (100 mL) over 15 minutes. The resulting mixture was stirred at −78° C. for an additional 15 minutes. A cooled (−78° C.) solution of iodine (12 g, 47 mmol, 1.5 equiv) in dry THF (72 mL) was poured rapidly into the reaction, and the resulting mixture was removed from the cold bath and stirred for 20s. The reaction was then quenched by the addition of saturated aq. NaS2O3. The reaction mixture was diluted with ethyl acetate, and organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (5% EtOAc, 95% hexanes) provided the title compound as a yellow solid (7.4 g, 82%) which was characterized by HNMR.

後処理

  1. additionwas poured rapidly into the reaction
  2. customthe resulting mixture was removed from the cold bath
  3. stirringstirred for 20s
  4. customThe reaction was then quenched by the addition of saturated aq. NaS2O3
  5. additionThe reaction mixture was diluted with ethyl acetate, and organic layer
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d2ebe01cf6a443ff8123095093c5c2c9
出典データセット
uspto-grants-2010_12
特許番号
US07851484B2

反応ノート

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