Benzoic Acid → HCID 59412516, compound

HRID 877292Notes

Reaction equation

HRID 877292 reaction equation
C1(C)C=CC=CC=1P([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])C1C=CC=CC=1C.BrC1[C:25]2[C:30]([C:31]([C:38]3[C:43]4=[CH:44][CH:45]=[C:46]5[C:55]([CH:54]=[C:53]6[C:48]([CH:49]=[CH:50][CH:51]=[CH:52]6)=C5Br)=[C:42]4[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.[C:57](O)(=O)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.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:58]1([C:57]2[C:33]3[C:32]([C:31]([C:38]4[C:43]5=[CH:44][CH:45]=[C:46]6[C:55]([CH:54]=[C:53]7[C:48]([CH:49]=[CH:50][CH:51]=[CH:52]7)=[C:21]6[C:16]6[CH:15]=[CH:20][CH:19]=[CH:18][CH:17]=6)=[C:42]5[CH:41]=[CH:40][CH:39]=4)=[C:30]4[C:25]=2[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

9

Reactant 4

HCID 243Benzoic AcidHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 86643580HCID 86643580, compound

Product 1

HCID 59412516HCID 59412516, compound

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 22.5 g (40 mmol) of the resultant 9-bromo-10-(7-bromobenz[a]anthracen-4-yl)-anthracene, 12.2 g (100 mmol) of benzoic 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 cooling, 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), three times with 100 ml of ethanol and finally dried. Recrystallisation five times from DMF (about 3 ml/g); sublimation (p=5×10−5 mbar, T=350° C.). Yield: 12.6 g (23 mmol), 46.0%, purity 99.9% (HPLC), Tg=171.8° C.

Workup

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  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), three times with 100 ml of ethanol
  6. customfinally dried
  7. customRecrystallisation five times from DMF (about 3 ml/g)
  8. customsublimation (p=5×10−5 mbar, T=350° C.)

Sources & evidence

ORD record
ord-b0a0d46f34f14c1e9496031b0fcc41b2
Source dataset
uspto-grants-2015_03
Patent number
US08986852B2

Reaction notes

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