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

HRID 62280노트

반응식

HRID 62280 반응식
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

참가 물질

5

반응물 3

HCID 12695HexafluoroacetoneHCID 693693,5-DibromopyridineHCID 178418918HCID 178418918, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-de549faf83f9467ea4dc00b39b5f40c3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446047B2

반응 노트

불러오는 중…