N-bromobutanimide → Ethyl 2-bromomethyl-3,4-dichlorobenzoate
Reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:3]1[C:2]([Cl:1])=[C:12]([Cl:13])[CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of ethyl 3,4-dichloro-2-methylbenzoate (34.0 g), N-bromosuccinimide (30.0 g) and carbon tetrachloride was irradiated with u.v. light in a photochemical reactor for 3 hours. The cooled mixture was filtered and the filtrate washed with water, dried (magnesium sulphate) and evaporated to give ethyl 2-bromomethyl-3,4-dichlorobenzoate (51.0 g) as an oil, NMR (CDCl3) 1.45 (t,3H), 4.4 (q,2H), 5.15 (s,2H), 7.7 (m,2H).