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

HRID 2179852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179852
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

Komponenten

11

Edukt 4

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

Produkt 1

HCID 867013502-(7-(10-(Naphthalen-1-yl)anthracen-9-yl)naphthalen-2-yl)triphenyleneAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 75806TricyclohexylphosphineKatalysatorHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

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”.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-74c621d6b176483aa3911e3d333dbeaf
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09070885B2

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