Potassium Carbonate → HCID 86720844, compound

HRID 1482174Notes

Reaction equation

HRID 1482174 reaction equation
Br[C:2]1[C:19]2[C:10](=[CH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:59][O:60][C:61]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1B(O)O)=[O:62].C(=O)([O-])[O-].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(O)C.C1(C)C=CC=CC=1>[CH3:59][O:60][C:61](=[O:62])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[C:9]1[C:10]2[C:19](=[CH:18][C:17]3[C:12]([CH:11]=2)=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:2]=[C:3]2[C:8]=1[CH:7]=[CH:6][CH:5]=[CH:4]2

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 27734962-(Methoxycarbonyl)benzeneboronic acidHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 713579985-Bromotetracene

Product 1

HCID 86720844HCID 86720844, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5-Bromotetracene (3.0 g, 9.77 mmol), tris(dibenzylideneacetone)dipalladium (448 mg, 0.489 mmol), (bis(2-diphenylphosphinophenyl)ether (1.05 g, 1.95 mmol), (2-(methoxycarbonyl)phenyl)boronic acid (3.52 g, 19.5 mmol) and potassium carbonate (5.40 g, 39.1 mmol) were added to a solvent mixture containing 200 mL of toluene, 12 mL of ethanol and 24 mL of water. The mixture was reacted under reflux at the boiling point for 24 hours in a nitrogen atmosphere to obtain methyl-2-(tetracen-5-yl)benzoate at a yield of 73%.

Workup

  1. customThe mixture was reacted
  2. temperatureunder reflux at the boiling point for 24 hours in a nitrogen atmosphere

Sources & evidence

ORD record
ord-cff8fdb46ee0464e8475fdb82f728b1f
Source dataset
uspto-grants-2016_08
Patent number
US09412952B2

Reaction notes

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