Ethanol → 12-(4-bromophenyl)-10,10-dimethyl-10H-indeno[2,1-b]triphenylene

HRID 1852557Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1([CH3:44])[C:34]2[C:14]([CH:15]=[C:16]3[CH:33]=[C:32]4[C:19]([C:20]5[C:25]([C:26]6[C:31]4=[CH:30][CH:29]=[CH:28][CH:27]=6)=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:18][C:17]3=2)=[CH:13][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11]1.C([O-])([O-])=O.[Na+].[Na+].CCO>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]2[CH:13]=[C:14]3[C:34]([C:10]([CH3:44])([CH3:9])[CH:11]=2)=[C:17]2[C:16]([CH:33]=[C:32]4[C:19](=[CH:18]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]4=2)=[CH:15]3)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6.6 g (28 mmol) of 1,4-dibromobenzene, 15.1 g (32 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetra methyl-1,3,2-dioxaborolane, 0.32 g (0.28 mmol) of tetrakis(triphenylphosphine) palladium, 22 ml of 2M Na2CO3, 60 ml of EtOH and 130 ml toluene was degassed and placed under nitrogen and then heated at 90° C. for 12 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 and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 7.4 g (53%) as a white solid.

Workup

customwas degassed
customthe reaction
temperatureto cool to room temperature
filtrationthe precipitated product was filtered off with suction
customthe residue was purified by column chromatography on silica (hexane-dichloromethane)

Sources & evidence

ORD record: ord-85e25a59d33a454da2cb3af87001bd09
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962160B2

Reaction notes

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