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

HRID 600105Notes

Reaction equation

HRID 600105 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>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[C:3]3[C:8]([C:9]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[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:25][CH:24]=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 45%

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 Pd(PPh3)4, 3 ml (6 mmol) of 2 mol/L potassium carbonate (K2CO3) solution, and 10 ml of toluene were 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 saline solution, then dried with magnesium sulfate. After natural filtration, the filtrate was concentrated, and recrystallized with chloroform and hexane. The target substance of 9-(4-bromophenyl)-10-phenylanthracene was obtained as a light brown solid, weighing 562 mg in a yield of 45% (synthesis scheme (j-6)).

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, then dried with magnesium sulfate
  5. filtrationAfter natural filtration
  6. concentrationthe filtrate was concentrated
  7. customrecrystallized with chloroform and hexane

Sources & evidence

ORD record
ord-223011d753b54f5e925b021ad2512d1f
Source dataset
uspto-grants-2011_03
Patent number
US07897964B2

Reaction notes

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