Dimethylformamide → 1-(3,5-Dichlorophenyl)-6-(4-methylphenyl)pyrene

HRID 1914400ノート

反応式

HRID 1914400 の反応式
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([Cl:32])[CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:25][C:26]1[CH:27]=[C:28]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:29]=[C:30]([Cl:32])[CH:31]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 27343313,5-Dichlorophenylboronic acidHCID 861013611-Bromo-6-(4-methylphenyl)pyrene

生成物 1

HCID 861013811-(3,5-Dichlorophenyl)-6-(4-methylphenyl)pyrene収率 58.4%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixed solution of 8.0 g of 1-bromo-6-(4-methylphenyl)pyrene, 4.5 g of 3,5-dichlorophenylboronic acid, 9.2 g of tripotassium phosphate, 1.4 g of tetrabutylammonium bromide, 97 mg of palladium acetate and 215 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 120° C. for 5 hours. The solution was cooled to room temperature and 1.0 L of water was poured into the solution, followed by extraction with 600 ml of dichloromethane. The organic layer was washed twice with 200 ml of water, dried over magnesium sulfate and then filtered through Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of ethyl acetate, and then the precipitated solid was collected by filtration. The precipitated solid was recrystallized from 100 ml of dimethylformamide and then vacuum-dried to obtain 5.5 g of 1-(3,5-dichlorophenyl)-6-(4-methylphenyl)pyrene.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 600 ml of dichloromethane
  3. washThe organic layer was washed twice with 200 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through Celite
  6. customThe filtrate was evaporated
  7. washthe residue was washed twice with 200 ml of ethyl acetate
  8. filtrationthe precipitated solid was collected by filtration
  9. customThe precipitated solid was recrystallized from 100 ml of dimethylformamide
  10. customvacuum-dried

出典と根拠

ORDレコード
ord-52661c09f5294f2fb52ef56def469bcd
出典データセット
uspto-grants-2013_12
特許番号
US08610345B2

反応ノート

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