N-bromobutanimide → 3-bromo-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole

HRID 1774066노트

반응식

HRID 1774066 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.C1C(=O)N([Br:28])C(=O)C1>ClCCl>[Br:28][C:17]1[CH:18]=[CH:19][C:20]2[N:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 588035919-(2-(2-methoxyethoxy)ethyl)-9H-carbazole

생성물 1

HCID 708962893-bromo-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1a (2 g, 7.4 mmol) in dichloromethane (60 mL) was added NBS (1.3 g, 7.4 mmol) portionwise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (EA:PE=1:5) as eluent to afford 2a (1.75 g) in 68% yield as an oil that can turn into solid after standing. 1H NMR (400 MHz, CDCl3) δ 8.16 (d, J=2.0 Hz, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.51 (dd, J=8.0 Hz, 2.0 Hz, 1H), 7.44 (m, 2H), 7.34 (d, J=8.4 Hz, 1H), 7.22 (m, 1H), 4.46 (t, J=6.0 Hz, 2H), 3.83 (t, J=6.0 Hz, 2H), 3.48 (m, 2H), 3.39 (m, 2H), 3.28 (s, 3H). 13C NMR (400 MHz, CDCl3) δ 140.7, 139.2, 128.2, 126.3, 124.5, 122.8, 121.8, 120.4, 119.3, 111.7, 110.4, 109.0, 71.8, 70.7, 69.1, 59.0, 43.2. MS (FAB) m/z Calcd for C17H18BrNO2 347.0 Found 347.3 [M]+.

후처리

  1. additionAfter complete addition
  2. washThe resulting solution was washed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-177a33b9105a4cfb86ef75a4d72ac319
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255933B2

반응 노트

불러오는 중…