N-Methylcarbazole → 3-bromo-9-methyl-9H-carbazole

HRID 1749241Notes

Reaction equation

HRID 1749241 reaction equation
[CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C1C(=O)N([Br:22])C(=O)C1>ClCCl>[Br:22][C:11]1[CH:12]=[CH:13][C:14]2[N:2]([CH3:1])[C:3]3[C:8]([C:9]=2[CH:10]=1)=[CH:7][CH:6]=[CH:5][CH:4]=3

Participants

4

Reactant 2

HCID 15142N-MethylcarbazoleHCID 67184N-bromobutanimide

Product 1

HCID 27290313-bromo-9-methyl-9H-carbazoleYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1b (2.5 g, 13.8 mmol) in dichloromethane (80 mL) was added NBS (2.4 g, 13.8 mmol) portion-wise 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=1:10) as eluent to afford 2b (2.11 g) in 59% yield. 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=2.0 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.54 (dd, J=8.8 Hz, J=2.0 Hz, 1H), 7.50 (td, J=8.0 Hz, J=1.2 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.27-7.22 (m, 2H), 3.82 (s, 3H).

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-4d1003deb57f45cd813d01ec520a55f0
Source dataset
uspto-grants-2015_10
Patent number
US09156814B2

Reaction notes

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