Ethanol → 10,10-dimethyl-12-(3-(pyren-1-yl)phenyl)-10H-indeno[1,2-b]triphenylene

HRID 1852553ノート

反応式

HRID 1852553 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:21]3[C:22]4=[C:23]5[C:18](=[CH:19][CH:20]=3)[CH:17]=[CH:16][CH:15]=[C:14]5[CH:13]=[CH:12][C:11]4=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:24][C:25]1([CH3:59])[C:49]2[C:29]([CH:30]=[C:31]3[CH:48]=[C:47]4[C:34]([C:35]5[C:40]([C:41]6[C:46]4=[CH:45][CH:44]=[CH:43][CH:42]=6)=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:33][C:32]3=2)=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26]1.C([O-])([O-])=O.[Na+].[Na+].CCO>CO.C1(C)C=CC=CC=1>[CH3:59][C:25]1([CH3:24])[C:49]2[C:29]([CH:30]=[C:31]3[C:32]=2[CH:33]=[C:34]2[C:47]([C:46]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[C:40]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=42)=[CH:48]3)=[CH:28][C:27]([C:6]2[CH:7]=[CH:2][CH:3]=[C:4]([C:8]3[C:21]4[C:22]5=[C:23]6[C:18](=[CH:19][CH:20]=4)[CH:17]=[CH:16][CH:15]=[C:14]6[CH:13]=[CH:12][C:11]5=[CH:10][CH:9]=3)[CH:5]=2)=[CH:26]1

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 578361411-(3-Bromophenyl)pyreneHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 8671831410,10-dimethyl-12-(3-(pyren-1-yl)phenyl)-10H-indeno[1,2-b]triphenylene収率 57%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A mixture of 5 g (14 mmol) of 1-(3-bromophenyl)pyrene, 7.53 g (16 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.16 g (0.14 mmol) of tetrakis(triphenyl phosphine)palladium, 11 ml of 2M Na2CO3, 30 ml of EtOH and 65 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 4 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 to give 4.95 g (yield 57%) of yellow product which was recrystallized from toluene. MS(m/z, FAB+): 620.1; 1H NMR (CDCl3, 400 MHz): chemical shift (ppm) 9.05 (s, 1H), 8.46˜8.41 (m, 2H), 8.40 (s, 1H), 8.06˜7.84 (m, 9H), 7.74 (d, J=8.00 Hz, 1H), 7.69˜7.59 (m, 4H), 7.54˜7.39 (m, 5H), 7.31˜7.16 (m, 3H), 1.82 (s, 6H).

後処理

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered off with suction

出典と根拠

ORDレコード
ord-407f4f5a7d484032bff8792d06b3ccd0
出典データセット
uspto-grants-2015_02
特許番号
US08962160B2

反応ノート

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