The bromination of benz[f]indanone and the synthesis of brom substitued benz[f]indanones

Key Words: photobromination, bromobenz[f]indanones, bromobenz[f]indenones Benz[f]indenones are potentially useful building blocks in organic and organometallic synthesis. However, their chemistry has not been extensively investigated. Recently, benz[f]indenones were used as important starting materials in the synthesis of kinamycin antibiotics, which showed excellent activity against grampositive bacteria. Benz[f]indenones and benz[f]indenes were used as target molecules for computational chemistry. In this work, bromination reactions of benz[f]indanone were investigated using different reaction conditions such as the presence of excess bromine, NBS, Lewis? acid catalyst, application of light or heat, etc. We prepared a variety of brominated derivatives (29, 31, 33, 37) and accomplished the first and quantitative synthesis of 2,3-dibromobenz[f]indenone (32). This molecule can serve as the key compound for the preparation of other substituted 2,3-disubstituted benz[f]indenone derivatives and benz[f]ninhydrine as well as for the construction of the dibenzo[c]flurenone skeleton.