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Benzo[a]carbazole → 11-(2-Ethylhexyl)-11H-benzo[a]carbazole

HRID 2203244
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HRID 2203244 반응식
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8]3.[H-].[Na+].Br[CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C=O>[CH2:27]([CH:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21][N:8]1[C:7]2[C:15](=[CH:16][CH:17]=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:6]3=2)[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:28]
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참가 물질

5

반응물 3

HCID 9196Benzo[a]carbazoleHCID 24758Sodium hydrideHCID 868042-Ethylhexyl bromide

생성물 1

HCID 6713010811-(2-Ethylhexyl)-11H-benzo[a]carbazole수율 101.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To 11H-benzo[a]carbazole (0.70 g; 3.22 mmol) in dimethyl formamide (DMF) (3 mL) is added sodium hydride (0.19 g; 4.67 mmol) at 0° C. After stirring for 1 h at 0° C., 1-bromo-2-ethylhexane (1.24 g; 6.44 mmol) is added at 0° C., and the mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water, and the crude product is extracted twice with AcOEt (acetic acid ethyl ester). The combined organic layer is washed with H2O and brine, dried over MgSO4, concentrated and dried in vacuo to give a yellow liquid as a crude product (1.08 g). The product is used for the next reaction without further purification. The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.80-0.92 (m, 6H), 1.16-1.47 (m, 8H), 2.27 (m, 1H), 4.65-4.69 (m, 2H), 7.27 (td, 1H), 7.44-7.59 (m, 4H), 7.66 (d, 1H), 8.02 (d, 1H), 8.14 (d, 1H), 8.18 (d, 1H), 8.54 (d, 1H).

후처리

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionthe crude product is extracted twice with AcOEt (acetic acid ethyl ester)
  3. washThe combined organic layer is washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-712a66078ddd4bb08fe0fa814babb9f9
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365515B2

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