Tetrabutylammonium Fluoride Trihydrate → 2-tert-Butyl-3-bromo-4-iodopyridine

HRID 921028ノート

反応式

HRID 921028 の反応式
[C:1]([C:5]1[C:10]([Br:11])=[C:9]([I:12])[CH:8]=[C:7]([Si](C)(C)C)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([C:5]1[C:10]([Br:11])=[C:9]([I:12])[CH:8]=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 679956892-Tert-butyl-3-bromo-4-iodo-6-trimethylsilylpyridine

生成物 1

HCID 679953862-tert-Butyl-3-bromo-4-iodopyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 14.8 g (36 mmol) of 2-tert-butyl-3-bromo-4-iodo-6-trimethylsilylpyridine and 14.0 g (40 mmol) of tetrabutylammonium fluoride trihydrate in 150 ml of THF is heated under reflux for 5 min. After cooling and removal of the THF in vacuo, the residue is taken up in 200 ml of dichloromethane, the org. phase is washed five times with 100 ml of water each time and dried over sodium sulfate. After removal of the dichloromethane in vacuo, the residue is recrystallised from ethanol. Yield: 9.2 g (27 mmol), 75%. Purity: >95% according to 1H-NMR.

後処理

  1. temperatureunder reflux for 5 min
  2. temperatureAfter cooling
  3. customremoval of the THF in vacuo
  4. washphase is washed five times with 100 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the dichloromethane in vacuo
  7. customthe residue is recrystallised from ethanol

出典と根拠

ORDレコード
ord-6a0d4bae482a48cabc4b03e1b291913c
出典データセット
uspto-grants-2016_03
特許番号
US09273080B2

反応ノート

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