Hexafluoroacetone → 2-(5-Bromopyridin-3-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 2199841ノート

反応式

HRID 2199841 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C([Mg]Cl)(C)C.[F:14][C:15]([F:23])([F:22])[C:16]([C:18]([F:21])([F:20])[F:19])=[O:17]>C1COCC1>[Br:8][C:6]1[CH:7]=[C:2]([C:16]([OH:17])([C:18]([F:21])([F:20])[F:19])[C:15]([F:23])([F:22])[F:14])[CH:3]=[N:4][CH:5]=1

参加物

5

反応物 3

HCID 12695HexafluoroacetoneHCID 693693,5-DibromopyridineHCID 178418918HCID 178418918、化合物

生成物 1

HCID 177589312-(5-Bromopyridin-3-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 3,5-dibromo pyridine 257 (1.09 g, 4.60 mmol) in dry THF cooled to 0° C., was added isopropyl magnesium chloride (2.4 mL, 4.8 mmol) drop wise while stirring for 10 min. Hexafluoroacetone (CF3—CO—CF3) 244 was added to the resulting reaction and continued stirring for another 2 h. After completion of the starting materials, the reaction was quenched with saturated ammonium chloride solution. The organic layer was separated and aqueous phase was extracted again with diethyl ether, the combined organic layer was dried over sodium sulphate and concentrated to get the crude 2-(5-bromopyridin-3-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol 258. The crude was purified through silica gel by using 100-200 mesh silica gel by eluting the compound at 20:5 ethyl acetate in hexane as thick oil of compound 258.

後処理

  1. stirringcontinued stirring for another 2 h
  2. customAfter completion of the starting materials, the reaction was quenched with saturated ammonium chloride solution
  3. customThe organic layer was separated
  4. extractionaqueous phase was extracted again with diethyl ether
  5. dry with materialthe combined organic layer was dried over sodium sulphate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d6d017eebcf40038d6217a43bf0ab65
出典データセット
uspto-grants-2016_06
特許番号
US09359315B2

反応ノート

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