Bromine → 5-bromo-N-ethoxalylindoline

HRID 52460Notes

Reaction equation

HRID 52460 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[Br:17]Br>ClCCl.[Fe]>[Br:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:1]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2])[CH2:9][CH2:10]2

Participants

5

Reactant 2

HCID 24408BromineHCID 1581489N-ethoxalylindoline

Product 1

HCID 100403095-bromo-N-ethoxalylindolineYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-ethoxalylindoline (4 g, 18.3 mmol), and iron powder (0.40 g) in dichloromethane (40 mL) was added dropwise bromine (1.43 mL, 27.7 mmol) at 0° C. The mixture was stirred for 4 h at room temperature and filtered. The filtrate was washed with aqueous sodium thiosulfate and then brine, dried over magnesium sulfate, and concentrated to give 5.24 g of 5-bromo-N-ethoxalylindoline (95%): 1H NMR (270 MHz, CDCl3) δ8.07(d, 1H, J=8 Hz), 7.35 (dd, 2H, J=8, 1 Hz), 4.38 (q, 2H, J=7 Hz), 4.27 (t, 2H, J=8 Hz), 3.20 (t, 2H, J=8 Hz), 1.41 (t, 3H, J=7 Hz).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with aqueous sodium thiosulfate
  3. dry with materialbrine, dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e02f945a230469eb53fd6a4da90e6b9
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

Loading…