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

HRID 2169681Notes

Reaction equation

HRID 2169681 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-phenylanthracene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

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 a potassium carbonate (K2CO3) aqueous solution (2 mol/L), and 10 mL of toluene were stirred at 80° C. for 9 hours. After the reaction, toluene was added therein, and the mixture was filtered through Florisil, Celite, and alumina. The filtrate was washed with water and a saturated saline solution and then dried with magnesium sulfate. After the solution was filtered naturally, the filtrate was concentrated and recrystallized with chloroform and hexane; thus, 562 mg of a light brown solid of 9-phenyl-10-(4-bromophenyl)anthracene that was an object was obtained (yield: 45%).

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered through Florisil, Celite, and alumina
  3. washThe filtrate was washed with water
  4. dry with materiala saturated saline solution and then dried with magnesium sulfate
  5. filtrationAfter the solution was filtered naturally
  6. concentrationthe filtrate was concentrated
  7. customrecrystallized with chloroform and hexane
  8. customwas obtained (yield: 45%)

Sources & evidence

ORD record
ord-898deb15d22e42f8b5140364b2978643
Source dataset
uspto-grants-2015_06
Patent number
US09048436B2

Reaction notes

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