Dimethylformamide → HCID 58259997、化合物

HRID 547845

反応式

HRID 547845 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 58259997HCID 58259997、化合物収率 75%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-dcf6c20a350d49929879bef76e6a13ee
出典データセット
uspto-grants-2011_05
特許番号
US07939569B1

関連ノート

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