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

HRID 877288Notes

Reaction equation

HRID 877288 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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.)

Sources & evidence

ORD record
ord-3291fcd3b72046f3a14682e4d68a54fb
Source dataset
uspto-grants-2015_03
Patent number
US08986852B2

Reaction notes

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