N-bromobutanimide → Ethyl 4-bromo-3-hydroxybenzenepropanoate

HRID 1948765Notes

Reaction equation

HRID 1948765 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[CH3:2].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:15])=[C:9]([OH:13])[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoate

Product 1

HCID 57633781Ethyl 4-bromo-3-hydroxybenzenepropanoateYield 16%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a −10° C. solution of 3-(3-hydroxy-phenyl)-propionic acid ethyl ester (2.0 g, 10.31 mmol) in chloroform (0.2 M, 51 mL) was added N-bromosuccinimide (1.93 g, 10.83 mmol). After stirring at RT overnight, the solution was concentrated in vacuo and purified by flash column chromatography (SiO2, 5% to 15% ethyl acetate/hexanes) to give the product as a colorless oil (0.45 g, 16%).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by flash column chromatography (SiO2, 5% to 15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-976ce7b0f4ee4f0ab3fe7078de343abd
Source dataset
uspto-grants-2013_03
Patent number
US08399517B2

Reaction notes

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