Toluene → 9-([1,1'-Biphenyl]-3-yl)-10-([2,2'-binaphthalen]-7-yl)anthracene

HRID 2179856Notes

Reaction equation

HRID 2179856 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]4[C:17]([C:18](Br)=[C:19]5[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]5)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1.[C:36]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:37](B(O)O)=[CH:38][CH:39]=[CH:40][CH:41]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>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.O.C(O)C>[C:36]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:37]=[CH:38][CH:39]=[C:40]([C:18]2[C:19]3[C:24]([C:11]([C:8]4[CH:9]=[C:10]5[C:5]([CH:4]=[CH:3][C:2]([C:26]6[CH:35]=[CH:34][C:33]7[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=7)[CH:27]=6)=[CH:1]5)=[CH:6][CH:7]=4)=[C:12]4[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]4)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:41]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 4589187Biphenyl-2-boronic acidHCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

Product 1

HCID 867013549-([1,1'-Biphenyl]-3-yl)-10-([2,2'-binaphthalen]-7-yl)anthraceneYield 21.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Under the nitrogen atmosphere, ([9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, m-biphenylboronic acid (1.4 g), Pd(PPh3)4] (0.1 g), potassium phosphate (1.7 g), and a mixture solvent (16 ml) of toluene and ethanol (toluene/ethanol=4/1 (volume ratio)) were added to a flask and refluxed for 10 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with water. The precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol, and washed further with ethyl acetate. The obtained crude product was purified by silica gel column chromatography (solvent: chlorobenzene). Finally, after re-crystallization with chlorobenzene, 9-([1,1′-biphenyl]-3-yl)-10-([2,2′-binaphthalen]-7-yl)anthracene (0.5 g) was obtained as the target compound represented by Formula (1-160). The scheme is shown in the following “Reaction 16”.

Workup

  1. temperaturerefluxed for 10 hours
  2. filtrationThe precipitates were collected by suction filtration
  3. washThe obtained solid was washed with water
  4. washwashed further with ethyl acetate
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (solvent: chlorobenzene)
  7. customFinally, after re-crystallization with chlorobenzene

Sources & evidence

ORD record
ord-050887ab92f246548c6b5e180aba4e8d
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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