Bromobenzene → 4-Phenylbenz[a]anthracene

HRID 877295Notes

Reaction equation

HRID 877295 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH:30]1[C:35]2=[C:36]3[C:45](=[CH:46][CH:47]=[C:34]2[C:33](B(O)O)=[CH:32][CH:31]=1)[CH:44]=[C:43]1[C:38]([CH:39]=[CH:40][CH:41]=[CH:42]1)=[CH:37]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:24]1([C:33]2[C:34]3=[CH:47][CH:46]=[C:45]4[C:36]([CH:37]=[C:38]5[C:43]([CH:42]=[CH:41][CH:40]=[CH:39]5)=[CH:44]4)=[C:35]3[CH:30]=[CH:31][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

9

Reactant 4

HCID 7961BromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 59412500Benz[a]anthracene-4-boronic acid

Product 1

HCID 594124904-Phenylbenz[a]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 7.8 g (50 mmol) of bromobenzene, 15.0 g (55 mmol) of benz[a]anthracene-4-boronic acid and 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.

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

Sources & evidence

ORD record
ord-f0a93e40f7db4c56aaa35044ecceb253
Source dataset
uspto-grants-2015_03
Patent number
US08986852B2

Reaction notes

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