5543-27-1

Example 40A Synthesis of (4-bromophenyl)pyrrolidin-1-ylmethanone: 4-bromobenzoyl chloride (3 g, 13.7 mmol) was dissolved in dichloromethane (25 mL) and cooled to 0°C. Pyrrolidine (2.5 mL, 30.3 mmol) and triethylamine (2 mL, 14.4 mmol) were added sequentially under stirring. The reaction mixture was slowly warmed up to room temperature over 3 hours. After completion of the reaction, the mixture was concentrated to remove the solvent. The crude product was purified by rapid chromatography on silica gel with an eluent gradient of 10-60% hexane/ethyl acetate to afford 4-(pyrrolizinylcarbonyl)bromobenzene (3.1 g, 89% yield). Mass spectrum (ESI) m/e 256 (M + H)+.

[1] Patent: US2007/259937, 2007, A1. Location in patent: Page/Page column 17
[2] Patent: US6340759, 2002, B1. Location in patent: Example 274
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 8, p. 1115 - 1121
[4] Organic Letters, 2015, vol. 17, # 19, p. 4850 - 4853