Potassium Carbonate → 9-Phenylanthracene

HRID 2075610Notes

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+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.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

First, 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 (abbr.: DME) were mixed and stirred at 80° C. for nine 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 saturated saline 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 as a target matter was obtained with a yield of 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 and saturated saline
dry with materialdried with magnesium sulfate
filtrationAfter the solution was filtered naturally
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-8552e4f098ef4f469d4d9812b1777384
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919773B2

Reaction notes

Loading…