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

HRID 2075613Notes

Reaction equation

HRID 2075613 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

First, 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 mixed and stirred at 80° C. for nine 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 saturated saline 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 as a target matter was obtained with a yield of 45%.

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered through Florisil, Celite, and alumina
  3. washThe filtrate was washed with water and saturated saline
  4. dry with materialdried with magnesium sulfate
  5. filtrationAfter the solution was filtered naturally
  6. concentrationthe filtrate was concentrated
  7. customrecrystallized with chloroform and hexane

Sources & evidence

ORD record
ord-55caa367fae5483db203f4854e9b82fa
Source dataset
uspto-grants-2011_04
Patent number
US07919773B2

Reaction notes

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