Ethyl bromoacetate → Ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate

Reaction equation

[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[Cl:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:6][C:5]=1[Cl:11]

Participants

Procedure

To a stirred solution of 4-(2-bromoethyl)-3-chlorophenol (158 mg) in acetone (7 ml) were added potassium carbonate (139 mg) and ethyl bromoacetate (89 μl) at room temperature. After the mixture was stirred for 20 hours at room temperature, the insoluble material was filtered off and the filtrate was concentrated in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate 7/1) gave ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate (193 mg).