Nitrogen → N-((1,1'-Biphenyl)-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine

HRID 2277355Notes

Reaction equation

N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.N#N.[C:17]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:22]=[CH:21][C:20]([NH:23][C:24]2[CH:36]=[CH:35][C:34]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]([CH3:38])([CH3:37])[C:26]=3[CH:25]=2)=[CH:19][CH:18]=1.[Br:45][C:46]1[CH:51]=[CH:50][C:49](I)=[CH:48][CH:47]=1>C1(C)C=CC=CC=1.[Cu]Cl.O>[C:17]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:22]=[CH:21][C:20]([N:23]([C:49]2[CH:50]=[CH:51][C:46]([Br:45])=[CH:47][CH:48]=2)[C:24]2[CH:36]=[CH:35][C:34]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]([CH3:38])([CH3:37])[C:26]=3[CH:25]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A degassed solution of 490 mg (0.16 mmol) of copper(I) chloride and 906 mg (5 mmol) of 1,10-phenanthroline in 100 ml of toluene is saturated with N2 for 1 h and heated to 130° C. 18 g (50 mmol) of N-[1,1-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-2-amine and 14 g (50 mmol) of 1-bromo-4-iodobenzene are subsequently added to the solution, which is then heated at 180° C. for 2 h. After cooling, 180 ml of water are added to the mixture, the organic phase is separated off, and the solvent is removed in vacuo. The product is recrystallised from n-hexane.

Workup

temperatureis then heated at 180° C. for 2 h
temperatureAfter cooling
customthe organic phase is separated off
customthe solvent is removed in vacuo
customThe product is recrystallised from n-hexane

Sources & evidence

ORD record: ord-9b6006e4cb1e4d71b1fe1619917ebad0
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133119B2

Reaction notes

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