N-bromobutanimide → Ethyl 3-(4-bromo-3-hydroxyphenyl)propanoate
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationthe solution was concentrated in vacuo
- custompurified by flash column chromatography (SiO2, 5% to 15% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-f0d5ac09597b4d6ca5b9c78acbcbeecc
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586631B2
Reaction notes
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