Ethanol → HCID 57548890, compound

HRID 1775396Notes

Reaction equation

[Br:1][C:2]1[C:3]2[C:8]([C:9](Br)=[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:17]1(B(O)O)[C:30]2[C:31]3=[C:32]4[C:27](=[CH:28][CH:29]=2)[CH:26]=[CH:25]C=C4[CH:22]=[CH:21][C:20]3=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:42][CH2:43]O>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:1][C:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]([C:10]2[C:11]3[C:32]4=[C:31]5[C:20](=[CH:21][CH:22]=3)[CH:19]=[CH:18][CH:17]=[C:30]5[CH:29]=[CH:28][C:27]4=[CH:26][CH:25]=2)=[C:14]2[C:15]=1[CH:42]=[CH:43][CH:12]=[CH:13]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 15 g (44.6 mmol) of 9,10-dibromoanthracene, 11 g (44.6 mmol) of pyren-1-ylboronic acid, 0.52 g (0.446 mmol) of Tetrakis(triphenylphosphine)palladium, 33 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After the reaction finish, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 8.8 g (43%) as a yellow solid.

Workup

customwas degassed
temperatureto cool to room temperature
extractionThe organic layer was extracted with ethyl acetate and water
dry with materialdried with anhydrous magnesium sulfate
customthe solvent was removed
customthe residue was purified by column chromatography on silica (hexane-dichloromethane)

Sources & evidence

ORD record: ord-601def5e7be94e4ab55f8ed50c9b6005
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260363B2

Reaction notes

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