[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17]([CH3:19])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]>C(Cl)(Cl)(Cl)Cl>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17]([CH2:19][Br:1])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]A solution of 38 g (0.24 mole) of bromine in 100 ml of CCl4 was added dropwise over 50 min to a stirred, refluxing mixture of 55 g (0.24 mole) of methyl 5-(p-nitrophenyl)-2-furyl ketone and 1200 ml of CCl4. After the addition was complete, the reaction mixture was heated under reflux for 3/4 hr and allowed to stand at room temperature overnight. The yellow solid was collected by filtration to give 69 g (93%) of bromomethyl 5-(p-nitrophenyl)-2-furyl ketone, m.p. 153°-162°.
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