Water → HCID 260376, compound

HRID 659918Notes

Reaction equation

HRID 659918 reaction equation
O.Br[C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2>C(C1C=CC(B(O)O)=CC=1)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:11]([C:13]1[CH:12]=[CH:11][C:16]([C:3]2[C:4]3[C:9]([CH:10]=[C:9]4[C:4]=2[CH:5]=[CH:6][CH:7]=[CH:8]4)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:15][CH:14]=1)([CH3:16])([CH3:12])[CH3:10]

Participants

8

Reactant 2

HCID 962WaterHCID 740629-Bromoanthracene

Product 1

HCID 260376HCID 260376, compoundYield 183.6%

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolventHCID 62657Potassium Phosphate, TribasicSolventHCID 167845palladium(II) acetateSolventHCID 27343204-tert-Butylphenylboronic acidSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 12 g of 9-bromoanthracene, 10 g of 4-tert-butylphenylboronic acid, 19.9 g of tripotassium phosphate, 3.02 g of tetrabutylammonium bromide and 106 mg of palladium acetate in 300 ml of dimethylformamide as a solvent was heated while stirred under nitrogen atmosphere at a temperature of 130° C. for 5 hours. After cooling the solution to room temperature, 400 ml of water was injected thereto and filtered. The solid separated by filtration was purified by silica gel column chromatography and vacuum dried to thereafter obtain 13.3 g of 9-(4′-tert-butylphenyl)anthracene.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. filtrationfiltered
  3. customThe solid separated by filtration
  4. customwas purified by silica gel column chromatography and vacuum
  5. customdried

Sources & evidence

ORD record
ord-91ebb49a7ad24636b795706a4fe86e75
Source dataset
uspto-grants-2011_12
Patent number
US08084146B2

Reaction notes

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