Dimethylformamide → HCID 58259997, 화합물

HRID 547845

반응식

HRID 547845 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1B(O)O.I[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 27831332,4,5-Trifluorophenylboronic acid

생성물 1

HCID 58259997HCID 58259997, 화합물수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A mixture of 2,4,5-trifluorophenylboronic acid (43.8 g, 249.2 mmol), 4-iodophenol (50 g, 226.5 mmol), potassium carbonate (78 g, 556.3 mmol), Pd(dppf)Cl2 methylene chloride complex (5.5 g, 6.8 mmol), DMF (150 mL), and water (38 mL) was degassed, purged with nitrogen, and heated at 50° C. overnight. The mixture was then diluted with EtOAc and water, acidified with conc. HCl under cooling with ice-water bath, stirred with charcoal, and filtered through Celite. The organic layer was separated, washed with water and brine, dried over sodium sulfate, filtered, and evaporated to afford a deep red oily crude product. The crude product in EtOAc was passed through silica gel to give 2′,4′,5′-trifluoro-biphenyl-4-ol as a light brown solid (38 g, 75%). LC-MS (ES) calculated for C12H7F3O, 224.18; found m/z 224 [M+H].

후처리

  1. customwas degassed
  2. custompurged with nitrogen
  3. additionThe mixture was then diluted with EtOAc and water
  4. temperatureunder cooling with ice-water bath
  5. filtrationfiltered through Celite
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto afford a deep red oily crude product

출처 및 근거

ORD 기록
ord-dcf6c20a350d49929879bef76e6a13ee
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

연결된 노트

불러오는 중…