[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(OCC)(=O)C>N(C(C)(C)C#N)=NC(C)(C)C#N.CCCCCC>[Br:16][CH2:15][C:14]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]To a mixture of ethyl 3-ethoxy-4-methylbenzoate (2.0 g), N-bromosuccinimide (1.9 g) and ethyl acetate (40 mL) was added 2,2′-azobis(2-methylpropionitrile) (15 mg), followed by stirring for 14 hours under heating with reflux. The mixture was left to be cooled, hexane was added thereto, the precipitated solid was separated by filtration, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane:5/95) to obtain ethyl 4-(bromomethyl)-3-ethoxybenzoate (2.4 g).
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