Potassium Carbonate → 9-[4-(Trifluoromethyl)phenyl]anthracene

HRID 1928973

Reaction equation

HRID 1928973 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:3]3[C:8]([CH:9]=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 740629-BromoanthraceneHCID 80271Tri-o-tolylphosphineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 2644639-[4-(Trifluoromethyl)phenyl]anthracene

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5.1 g (20 mmol) of 9-bromoanthracene, 3.8 g (20 mmol) of 4-trifluoromethylphenylboronic acid, and 244 mg (0.8 mmol) of tri(o-tolyl)phosphine were put into a 100-mL three-neck flask, and nitrogen substitution in the system was carried out. 20 mL of ethylene glycol dimethyl ether (DME) was added to this mixture, and the mixture was stirred under reduced pressure and degassed. After that, 45 mg (0.20 mmol) of palladium acetate(II) and 10 mL (2.0 mol/L) of a potassium carbonate solution were added. This reaction mixture was stirred at 80° C. for 3 hours under nitrogen gas stream. Then, the reaction mixture was cooled to the room temperature, and a solid that was precipitated was collected by suction filtration. The collected solid was dissolved in toluene, and the solution was subjected to suction filtration through Florisil, celite, and then alumina. The filtrate was condensed to obtain a solid, and the solid was recrystallized with ethanol, whereby 5.7 g of a white powdery solid, which was a target matter, was obtained with the yield of 88%.

Workup

  1. customdegassed
  2. stirringThis reaction mixture was stirred at 80° C. for 3 hours under nitrogen gas stream
  3. customa solid that was precipitated
  4. filtrationwas collected by suction filtration
  5. dissolutionThe collected solid was dissolved in toluene
  6. filtrationthe solution was subjected to suction filtration through Florisil, celite
  7. customcondensed
  8. customto obtain a solid
  9. customthe solid was recrystallized with ethanol, whereby 5.7 g of a white powdery solid, which
  10. customwas obtained with the yield of 88%

Sources & evidence

ORD record
ord-96fba1c7889646d8b748e68a0cdffc0b
Source dataset
uspto-grants-2012_05
Patent number
US08183793B2

Linked notes

Loading…