Ethyl 1H-indole-3-acetate → Ethyl (2-bromo-1H-indol-3-yl)acetate

HRID 2187629Notes

Reaction equation

HRID 2187629 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:2]1.C1C(=O)N([Br:23])C(=O)C1>ClCCl>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[Br:23])[CH3:15]

Participants

4

Reactant 2

HCID 13067Ethyl 1H-indole-3-acetateHCID 67184N-bromobutanimide

Product 1

HCID 53994886Ethyl (2-bromo-1H-indol-3-yl)acetateYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 15.0 g (73.8 mmol) of ethyl (indol-3-yl)acetate in 75 ml of anhydrous dichloromethane at 0° C. was added 13.1 g (73.8 mmol) of NBS in small portions. The mixture was stirred at 0° C. for 3 h and then quickly concentrated under reduced pressure (argon was used to normalize the pressure after concentration to avoid decomposition due to the product's instability). Column chromatography with 99:1 toluene/ethanol afforded 10.5 g (50%) of the 2-bromoindole as a yellow oil.

Workup

  1. concentrationquickly concentrated under reduced pressure (argon
  2. concentrationafter concentration

Sources & evidence

ORD record
ord-7aa27b926a1d4a05b2d9e576a7f2d465
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

Loading…