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

HRID 1027319ノート

反応式

HRID 1027319 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](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[C:4](Br)[CH:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=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>[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([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:2]3[CH:15]=[CH:16][C:5]([CH3:6])=[CH:4][CH:3]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[C:4]([C:11]3[CH:10]=[CH:9][C:8]([CH3:7])=[CH:17][CH:12]=3)[CH:3]=2)=[CH:23][CH:22]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 30159691,3,6-Tribromopyrene

生成物 1

HCID 866285911,3,6-Tri(4-methylphenyl)pyrene収率 167.2%

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
130 °C

実験手順

Next, a mixed solution of 2.0 g of 1,3,6-tribromopyrene, 2.5 g of 4-methylphenylboronic acid, 5.8 g of tripotassium phosphate, 0.88 g of tetrabutylammonium bromide, 61 mg of palladium acetate and 137 ml of deaerated dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 9 hours. After cooling to room temperature, 800 ml of water was injected, followed by extraction with 200 ml of dichloromethane. The organic layer was washed twice with 100 ml of water, dried over magnesium sulfate and then evaporated. The resultant concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 1.8 g of 1,3,6-tri(4-methylphenyl)pyrene as a pale yellow powder.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with 200 ml of dichloromethane
  3. washThe organic layer was washed twice with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. concentrationThe resultant concentrate
  7. customwas purified by silica gel column chromatography
  8. customvacuum-dried

出典と根拠

ORDレコード
ord-e068d6f8c028407fb4c7585fa03d15f9
出典データセット
uspto-grants-2014_05
特許番号
US08729530B2

反応ノート

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