Facile and efficient bromination of benz[F]Indan-1-One

The bromination reaction of benz[f]indan-1-one was investigated by nbs,molecular bromine and fotobromination. benz[f]indan-1-one was synthesized by treatment of α,α,α',α'- tetrabromo-o-xylene with cyclopenten-1-one. bromination of benz[f]indan-1-one with bromine (1.2 equiv) at low temperature afforded the α-monobromobenz[f]indanone in addition to α,α'- dibromobenz[f]indanone. the quantitative yield of α,α'-dibromobenz[f]indanone was synthesized by treatment of benz[f]indan-1-one with 2.1 equv. bromine at room temperature for 25 min. the electrophonic bromination of α,α'-dibromobenz[f]indanone with n-bromosuccinimide (nbs) regioselectively proceeded at c-8 side and afforded the corresponding 2,2,8- tribromobenz[f]indanone which also could be obtained from the treatment of benz[f]indan-1-one with nbs and sio 2. dibromobenz[f]indenone was generated by the treatment of benz[f]indan-1-one with bromine in photochemical reaction apparatus irradiated by 150 watt projection lamp. dibromobenz[f]indenone was also synthesized by the treatment of α,α'-dibromobenz[f]indanone with nbs in photochemical reaction apparatus irradiated by 150 watt projection lamp. 2,8- dibromobenz[f]indanone was synthesized by the reaction of α-monobromobenz[f]indanone with nbs.