Synthesis
General procedure for the synthesis of 1-(4-bromophenyl)cyclopropanecarboxylic acid from 1-(4-bromophenyl)cyclopropanecarbonitrile: A mixture of 1-(4-bromophenyl)cyclopropanecarbonitrile (7.5 g, 33.78 mmol), potassium hydroxide (7.6 g, 135 mmol), and ethylene glycol (50 mL) was heated to 160 °C for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature, water (200 mL) was added and the pH was adjusted to 3~4 with dilute hydrochloric acid to acidify the reaction mixture. Subsequently, the product was precipitated with 2N hydrochloric acid. The precipitate was collected by filtration to afford 1-(4-bromophenyl)cyclopropanecarboxylic acid (5.6 g, 69% yield). Mass spectrum (ESI) m/z (M+H)+ 240.
References
[1] Patent: US6359135, 2002, B1. Location in patent: Page column 113
[2] Patent: US6369225, 2002, B1. Location in patent: Page column 42, 112
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 16, p. 6003 - 6017
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 887 - 892
[5] Patent: WO2013/25733, 2013, A1. Location in patent: Paragraph 0490
