Potassium Carbonate → 9-Phenylanthracene

HRID 1967880Notes

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: 90 °C

Procedure

25.4 g (100 mmol) of 9-bromoanthracene, 12.8 g (105 mmol) of phenylboronic acid, 0.233 g (1.00 mmol) of palladium (II) acetate, and 0.913 g (3.00 mmol) of tri(ortho-tolyl)phosphine were put into a 500 mL three-necked flask. Then, the atmosphere in the flask was substituted with nitrogen. Thereafter, 100 mL of ethylene glycol dimethyl ether (abbreviation: DME) and 75 mL (150 mmol) of potassium carbonate solution (2.0 mol/L) were added to the mixture, and this mixture was refluxed at 90° C. for 6 hours to be reacted. After the reaction, a precipitate in the reaction mixture was collected by suction filtration. The obtained solid was recrystallized by a mixed solvent of chloroform and hexane; then 20.8 g of objective 9-phenylanthracene was obtained as a white powdered solid in a yield of 82%. A synthetic scheme of 9-phenylanthracene is illustrated below (synthetic scheme b-1).

Workup

customto be reacted
customAfter the reaction
filtrationa precipitate in the reaction mixture was collected by suction filtration
customThe obtained solid was recrystallized by a mixed solvent of chloroform and hexane

Sources & evidence

ORD record: ord-54b26edaf8e74cb78b6f2662510b781d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420874B2

Reaction notes

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