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

HRID 877288노트

반응식

HRID 877288 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-3291fcd3b72046f3a14682e4d68a54fb
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08986852B2

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