Potassium Phosphate, Tribasic → 9-(Phenyl)-10-(benz[a]anthracen-5-yl)-anthracene

HRID 877288ノート

反応式

HRID 877288 の反応式
[C:1]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[C:25]2[C:30]([C:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[C:32]3[C:37]=1[CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:29][CH:28]=[CH:27][CH:26]=2.[CH:44]1[C:49]2[C:50]3[C:59]([CH:60]=C(B(O)O)[C:48]=2[CH:47]=[CH:46][CH:45]=1)=[CH:58][C:57]1[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH:51]=3.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:38]1([C:31]2[C:32]3[C:37]([C:24]([C:1]4[CH:60]=[C:59]5[C:50]([CH:51]=[C:52]6[C:57](=[CH:58]5)[CH:56]=[CH:55][CH:54]=[CH:53]6)=[C:49]5[CH:44]=[CH:45][CH:46]=[CH:47][C:48]=45)=[C:25]4[C:30]=2[CH:29]=[CH:28][CH:27]=[CH:26]4)=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 41558369-Bromo-10-phenyl-anthraceneHCID 59412514Benz[a]anthracene-5-boronic acid

生成物 1

HCID 585361109-(Phenyl)-10-(benz[a]anthracen-5-yl)-anthracene

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒

実験手順

913 mg (3 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a well-stirred suspension of 16.7 g (50 mmol) of 9-bromo-10-(phenyl)anthracene, 15.0 g (55 mmol) of benz-[a]anthracene-5-boronic acid, 25.5 g (120 mmol) of tripotassium phosphate in a mixture of 300 ml of toluene, 100 ml of dioxane and 400 ml of water, and the mixture is subsequently heated under reflux for 16 h. After the mixture has been cooled, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol, recrystallised three times from DMF (about 7 ml/g) and subsequently sublimed twice (p=5×10−5 mbar, T=320° C.). Yield: 16.3 g (34 mmol), 67.8%, purity 99.9% (HPLC), Tg=150.0° C.

後処理

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter the mixture has been cooled
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  6. customrecrystallised three times from DMF (about 7 ml/g)
  7. custom(p=5×10−5 mbar, T=320° C.)

出典と根拠

ORDレコード
ord-3291fcd3b72046f3a14682e4d68a54fb
出典データセット
uspto-grants-2015_03
特許番号
US08986852B2

反応ノート

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