N-bromobutanimide → HCID 54103301, compound

HRID 1069653Notes

Reaction equation

HRID 1069653 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=1)[CH3:2].[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:7]=1[Br:25])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10805854HCID 10805854, compound

Product 1

HCID 54103301HCID 54103301, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester (10.8 g, 32 mmol) and 6.3 g (35 mmol) of N-bromosuccinimide in 250 mL of carbon tetrachloride was stirred for 1.5 hours, washed with Na2S2O3 solution, water, brine, and dried (Na2SO4). After concentrating at reduced pressure, the residue was chromatographed on silica gel and eluted with a gradient, 25% ether/hexane→40% ether/hexane, to give 5.5 g (43% yield) of 2-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester.

Workup

  1. washwashed with Na2S2O3 solution, water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationAfter concentrating at reduced pressure
  4. customthe residue was chromatographed on silica gel
  5. washeluted with a gradient, 25% ether/hexane→40% ether/hexane

Sources & evidence

ORD record
ord-536d23711a8d47eaab6ccf3b30f6fc29
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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