Toluene → 2-(7-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl)triphenylene

HRID 2179852Notes

Reaction equation

HRID 2179852 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]3[C:18]4[C:23]([C:24]([C:31]5[C:40]6[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=6)[CH:34]=[CH:33][CH:32]=5)=[C:25]5[C:30]=3[CH:29]=[CH:28][CH:27]=[CH:26]5)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[CH:43]1[C:60]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:47]=2[CH:46]=[CH:45][C:44]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>ClC1C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.CO.O.C(O)C>[C:31]1([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]([C:11]3[CH:10]=[C:9]4[C:14]([CH:15]=[CH:16][C:7]([C:44]5[CH:45]=[CH:46][C:47]6[C:48]7[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=7)[C:54]7[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=7)[C:60]=6[CH:43]=5)=[CH:8]4)=[CH:13][CH:12]=3)=[C:18]3[C:23]=2[CH:22]=[CH:21][CH:20]=[CH:19]3)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

11

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 59805119Triphenylen-2-ylboronic acidHCID 867013487-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate

Product 1

HCID 867013502-(7-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl)triphenyleneYield 55.8%

Reagents, catalysts & solvents 6

HCID 75806TricyclohexylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Procedure

Under the nitrogen atmosphere, 7-(10-(naphthalen-1-yl) anthracen-9-yl)naphthalen-2-yl trifluoromethane sulfonate (3.0 g) as the fifth intermediate compound, 2-triphenylene boronic acid (2.1 g), Pd(dba)2 (0.03 g), tricyclohexyl phosphine (0.03 g), potassium phosphate (2.2 g), and a mixture solvent (22 ml) of toluene, ethanol and water (toluene/ethanol/water=9/1/1 (volume ratio)) were added to a flask and refluxed for 2 hours. Once the heating is completed, the reaction solution was cooled to room temperature and added with methanol. 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 dissolved in chlorobenzene, and colored components were removed by passing through a silica gel short column. After re-crystallization with chlorobenzene, 2-(7-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl)triphenylene (1.9 g) was obtained as the target compound represented by Formula (1-38). The scheme is shown in the following “Reaction 10”.

Workup

  1. temperaturerefluxed for 2 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. customcolored components were removed
  7. customAfter re-crystallization with chlorobenzene

Sources & evidence

ORD record
ord-74c621d6b176483aa3911e3d333dbeaf
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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