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Ethanol → HCID 90302175, 화합물

HRID 2169689
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HRID 2169689 반응식
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[CH3:31][C:32]1([CH3:66])[C:56]2[C:36]([CH:37]=[C:38]3[CH:55]=[C:54]4[C:41]([C:42]5[C:47]([C:48]6[C:53]4=[CH:52][CH:51]=[CH:50][CH:49]=6)=[CH:46][CH:45]=[CH:44][CH:43]=5)=[CH:40][C:39]3=2)=[CH:35][C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33]1.C([O-])([O-])=O.[Na+].[Na+].CCO>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.CO.C1(C)C=CC=CC=1>[CH3:66][C:32]1([CH3:31])[C:56]2[C:36]([CH:37]=[C:38]3[C:39]=2[CH:40]=[C:41]2[C:54]([C:53]4[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=4[C:47]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=42)=[CH:55]3)=[CH:35][C:34]([C:2]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[CH:18][CH:17]=3)=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)=[CH:33]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86727987HCID 86727987, 화합물

생성물 1

HCID 90302175HCID 90302175, 화합물수율 63%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 887Methanol용매
HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A mixture of 6.5 g (14 mmol) of 2-(4-(10-bromoanthracen-9-yl)naphthalene-1-yl)thiophene, 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(triphenylphosphine)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 6.4 g (yield 63%) of yellow product which was recrystallized from toluene. MS (m/z, FAB+): 728.1; 1H NMR (CDCl3, 400 MHz): chemical shift (ppm) 9.13 (s, 1H), 8.64˜8.56 (m, 3H), 8.31˜8.05 (m, 5H), 7.95˜7.83 (m, 9H), 7.68˜7.61 (m, 2H), 7.55 (d, J=8.00 Hz, 1H), 7.49˜7.40 (m, 6H), 7.18 (d, J=6.20 Hz, 1H), 7.02 (t, J=6.20 Hz, 1H), 6.55 (d, J=8.00 Hz, 1H), 1.81 (s, 6H).

후처리

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

출처 및 근거

ORD 기록
ord-6e4ff6f228cb45ebb081ed6f844d93b6
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09048437B2

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