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

HRID 1749240ノート

反応式

HRID 1749240 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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. 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]+.

後処理

  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

出典と根拠

ORDレコード
ord-f4ac9c1d733c4a8fae4e648ca7812f51
出典データセット
uspto-grants-2015_10
特許番号
US09156814B2

反応ノート

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