Synthesis
General procedure for the synthesis of 3-bromo-1-indanone from 1-indanone: 264 g (2.2 mol) of 1-indanone was dissolved in 154 mL of carbon tetrachloride, and 390 g (2.2 mol) of N-bromosuccinimide (non-caking powder) and 0.5 g of benzoyl peroxide were added. The reaction was refluxed under mechanical stirring for 1.5 hours. During the reaction, the color of the mixture changed abruptly to yellow and all N-bromosuccinimides (density greater than carbon tetrachloride) were converted to succinimides (density less than carbon tetrachloride). After completion of the reaction, the mixture was cooled to 20 °C, filtered and concentrated in vacuum. The crude product, 3-bromo-1-indanone, was dissolved in 600 mL of ethyl acetate/heptane (1:2) solvent mixture, cooled in an ice bath for 2 h, and subsequently crystallized in a refrigerator overnight to give 257 g of 3-bromo-1-indanone crystals in 62% yield.
References
[1] Tetrahedron, 1995, vol. 51, # 32, p. 8953 - 8958
[2] Indian journal of chemistry, 1981, vol. 20 B, # 4, p. 303 - 307
[3] Patent: US2008/58329, 2008, A1. Location in patent: Page/Page column 13
[4] Tetrahedron Letters, 2006, vol. 47, # 7, p. 1097 - 1099
[5] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
