Ethanol → 12-(5-bromo-2-nitrophenyl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene

HRID 879915Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](I)[CH:3]=1.[CH3:12][C:13]1([CH3:47])[C:37]2[C:17]([CH:18]=[C:19]3[CH:36]=[C:35]4[C:22]([C:23]5[C:28]([C:29]6[C:34]4=[CH:33][CH:32]=[CH:31][CH:30]=6)=[CH:27][CH:26]=[CH:25][CH:24]=5)=[CH:21][C:20]3=2)=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14]1.C([O-])([O-])=O.[Na+].[Na+].CCO>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.CO.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:15]2[CH:16]=[C:17]3[C:37]([C:13]([CH3:47])([CH3:12])[CH:14]=2)=[C:20]2[C:19]([CH:36]=[C:35]4[C:22](=[CH:21]2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:34]4=2)=[CH:18]3)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7.5 g (22.8 mmol) of 4-bromo-2-iodo-1-nitrobenzene, 10.7 g (22.8 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.29 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium, 17 ml of 2M Na2CO3, 40 ml of EtOH and 100 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. Than 500 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 7 g (yield 57%) of yellow product which was recrystallized from toluene.

Workup

customwas degassed
customthe reaction
temperatureto cool to room temperature
filtrationthe precipitated product was filtered off with suction

Sources & evidence

ORD record: ord-e68ef33c2b1c4b18b940d6d10491983e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993130B2

Reaction notes

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