Bromine → HCID 13042092, compound

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:9][C:8]=1[Cl:17])C.[Br:19]Br>CO.Cl>[Cl:17][C:8]1[CH:9]=[C:10]([C:13](=[O:16])[CH:14]([Br:19])[CH3:15])[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([O:3][CH3:1])=[O:18]

Participants

Procedure

Ethyl-2-(2-chloro-4-propionylphenoxy)acetate(4 g) was dissolved in methanol (40-50 ml). HCl (2 drops, conc) was added, followed by the dropwise addition over 5-10 minutes of bromine (2.62 g, 0.016 mole). After the bromine addition was complete the mixture was heated on a steam bath for 15-30 minutes allowing much of the solvent to evaporate. The residue was washed with cold water and the remaining solid recrystallized several times from hexane to give methyl 2-[2-chloro-4-(2-bromopropionyl)phenoxy]acetate (4.6 g, 90%, mp 63°-65° C.