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

HRID 1477330Notes

Reaction equation

HRID 1477330 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-16f625140f31475ea8e1529eb064c52e
Source dataset
uspto-grants-2016_08
Patent number
US09403794B2

Reaction notes

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