Toluene → HCID 58526351, compound

HRID 2371238Notes

Reaction equation

HRID 2371238 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[CH:42]=[CH:41][C:27]2[CH:28]=[CH:29][C:30]3[CH:31]=[CH:32][C:33]4[CH:34]=[CH:35][C:36](Br)=[CH:37][C:38]=4[C:39]=3[C:26]=2[CH:25]=1.[C:43]1(B(O)O)[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][CH:44]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:64]1(C)[CH:69]=CC=[CH:66][CH:65]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:43]1([C:42]2[CH:41]=[CH:69][C:64]3[CH:65]=[CH:66][C:27]4[CH:28]=[CH:29][C:30]5[CH:31]=[CH:32][C:33]([C:34]6[C:6]7[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=7)[CH:37]=[CH:36][CH:35]=6)=[CH:38][C:39]=5[C:26]=4[C:25]=3[CH:24]=2)[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][CH:44]=1

Participants

9

Reactant 5

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 2545321-Naphthaleneboronic acidHCID 58526417HCID 58526417, compound

Product 1

HCID 58526351HCID 58526351, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 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 vigorously stirred suspension of 19.3 g (50 mmol) of 2,11-dibromobenzo[c]phenanthrene, 22.4 g (130 mmol) of 1-naphthaleneboronic 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 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 and recrystallised three times from DMF (about 10 ml/g). Yield: 14.4 g (30 mmol), 60.0%, purity 99.9% (HPLC).

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 10 ml/g)

Sources & evidence

ORD record
ord-47508d22439f43b2a8db2f25dfa5cf27
Source dataset
uspto-grants-2014_04
Patent number
US08710284B2

Reaction notes

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