Bromine → HCID 18344919, compound

HRID 2301327Notes

Reaction equation

HRID 2301327 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=2)[NH:8][C:7]=1[CH3:21])=[O:5])[CH3:2].[Br:22]Br>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:22])=[C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=2)[NH:8][C:7]=1[CH3:21])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 113237171H-Indole-5-acetic acid, 3-(ethoxycarbonyl)-2-methyl-, ethyl ester

Product 1

HCID 18344919HCID 18344919, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-ethoxycarbonylmethyl-2-methyl-1H-indole-3-carboxylic acid ethyl ester (3 g, 10.4 mmol) in acetic acid (20 mL) is added bromine (1.65 g, 10.4 mmol) dropwise, and the reaction mixture is stirred for 10 minutes. The solution is then concentrated in vacuo and chromatographed with a gradient of hexane/ethyl acetate (5%-30%) within 30 minutes to afford a yellow solid (3.3 g, 86%). MS: 368, 370 (M+1)+.

Workup

  1. concentrationThe solution is then concentrated in vacuo
  2. customchromatographed with a gradient of hexane/ethyl acetate (5%-30%) within 30 minutes

Sources & evidence

ORD record
ord-777d3381a8704e4fb877dee0fc6a0d2c
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

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