Potassium Carbonate → 9-Phenylanthracene

HRID 2360743Notes

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.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[C:16]1([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:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5.4 g (21.1 mmol) of 9-bromoanthracene, 2.6 g (21.1 mmol) of phenylboronic acid, 60 mg (0.21 mmol) of palladium acetate (Pd(OAc)2), 10 mL (20 mmol) of a potassium carbonate (K2CO3) aqueous solution (2 mol/L), 263 mg (0.84 mmol) of tri(o-tolyl)phosphine (P(o-tolyl)3), and 20 mL of 1,2-dimethoxyethane (abbreviation: DME) were mixed and stirred at 80° C. for 9 hours. After the reaction, the precipitated solid was collected by suction filtration, dissolved in toluene, and 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 and the filtrate was concentrated, 21.5 g of a light brown solid of 9-phenylanthracene that was an object was obtained (yield: 85%).

Workup

customAfter the reaction
filtrationthe precipitated solid was collected by suction filtration
dissolutiondissolved in toluene
filtrationfiltered through Florisil, Celite, and alumina
washThe filtrate was washed with water
dry with materiala saturated saline solution and then dried with magnesium sulfate
filtrationAfter the solution was filtered naturally
concentrationthe filtrate was concentrated
customwas obtained (yield: 85%)

Sources & evidence

ORD record: ord-92bcef3aaccc4359bd71a66261fae589
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686159B2

Reaction notes

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