N-bromobutanimide → 3-bromomethyl-9H-xanthen-9-one
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[Br:17]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 3-methyl-9H-xanthen-9-one (1.62 g, 7.71 mmol), N-bromosuccinic acid imide (1.37 g, 7.71 mmol), benzoyl peroxide (93 mg, 0.39 mmol) and carbon tetrachloride (15 ml) was heated under reflux for 15 hours. The insoluble matter was removed by filtration and the resulting filtrate was concentrated under a reduced pressure to give 3-bromomethyl-9H-xanthen-9-one (2.19 g, 7.57 mmol, 98%) as colorless crystals.