Sodium Hydroxide → Tris(2-bromo-6-pyridyl)fluoromethane

HRID 13637

反応式

HRID 13637 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:17]2[N:22]=[C:21]([Br:23])[CH:20]=[CH:19][CH:18]=2)([C:10]2[N:15]=[C:14]([Br:16])[CH:13]=[CH:12][CH:11]=2)O)[N:3]=1.C(N(S(F)(F)[F:30])CC)C.[OH-].[Na+]>ClCCl.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:17]2[N:22]=[C:21]([Br:23])[CH:20]=[CH:19][CH:18]=2)([C:10]2[N:15]=[C:14]([Br:16])[CH:13]=[CH:12][CH:11]=2)[F:30])[N:3]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 123472(Diethylamino)sulfur trifluorideHCID 53880796Tris(6-bromopyridin-2-yl)methanol

生成物 1

HCID 58036607Tris(2-bromo-6-pyridyl)fluoromethane

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

A solution of 50.0 g (100 mmol) of tris(2-bromo-6-pyridyl)methanol in 750 ml of dichloromethane was admixed with good stirring dropwise with 47.3 ml (400 mmol) of diethylaminosulfur trifluoride. Subsequently, the reaction mixture was heated under reflux for 30 min, then cooled to 5° C., and admixed with good stirring (highly exothermic!!!) with 300 ml of water and then with a solution of 64.0 g (1600 mmol) of sodium hydroxide in 600 ml of water (highly exothermic!!!). The organic phase was removed, the aqueous phase was washed twice with 200 ml of dichloromethane, and the combined organic phases were dried over calcium chloride and subsequently freed of dichloromethane. The remaining red-brown crystal slurry was taken up in 100 ml of methanol and filtered off. After washing with methanol, the colorless to beige crystals were dried under reduced pressure. The yield was 47.4 g (91.3%) at a purity of greater than 99.0% by 1H NMR.

後処理

  1. temperatureSubsequently, the reaction mixture was heated
  2. temperatureunder reflux for 30 min
  3. customThe organic phase was removed
  4. washthe aqueous phase was washed twice with 200 ml of dichloromethane
  5. dry with materialthe combined organic phases were dried over calcium chloride
  6. filtrationfiltered off
  7. washAfter washing with methanol
  8. customthe colorless to beige crystals were dried under reduced pressure

出典と根拠

ORDレコード
ord-a4921898052e487cb961c314a7687d52
出典データセット
uspto-grants-2010_06
特許番号
US07728137B2

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