Potassium Carbonate → 9-(4-Bromophenyl)-10-phenylanthracene

HRID 2369626Notes

Reaction equation

HRID 2369626 reaction equation
I[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Br:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:16]1([C:9]2[C:10]3[C:15]([C:2]([C:26]4[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][CH:25]=4)=[C:3]4[C:8]=2[CH:7]=[CH:6][CH:5]=[CH:4]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 149583739-Iodo-10-phenylanthracene

Product 1

HCID 221382759-(4-Bromophenyl)-10-phenylanthraceneYield 52.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

1.0 g (2.63 mmol) of 9-iodo-10-phenylanthracene, 542 mg (2.70 mmol) of p-bromophenylboronic acid, 46 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4), 3 mL (6 mmol) of an aqueous potassium carbonate (K2CO3) solution (2 mol/L), and 10 mL of toluene were collected, mixed, and stirred for 9 hours at 80° C. After the reaction, toluene was added and the mixture was filtered through florisil, Celite®, and alumina. The filtrate was washed with water and a saturated aqueous sodium chloride solution and then dried with magnesium sulfate. After natural filtration, the filtrate was concentrated and the obtained solid was recrystallized with chloroform and hexane, thereby obtaining 562 mg of objective 9-phenyl-10-(4-bromophenyl)anthracene as a light-brown solid with a yield of 45%.

Workup

  1. additionmixed
  2. additionwas added
  3. filtrationthe mixture was filtered through florisil, Celite®, and alumina
  4. washThe filtrate was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution and then dried with magnesium sulfate
  6. filtrationAfter natural filtration
  7. concentrationthe filtrate was concentrated
  8. customthe obtained solid was recrystallized with chloroform and hexane

Sources & evidence

ORD record
ord-ec7029b0ebf44633a6336779a349cc16
Source dataset
uspto-grants-2014_04
Patent number
US08704242B2

Reaction notes

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