Synthesis
Step 1: Preparation of 1-phenylcyclopropanecarbonitrile
To a stirred mixture of phenylacetonitrile (100 g, 0.8547 mol) dissolved in aqueous KOH (447 g, dissolved in 420 mL of water) and 2.7 g of tetrabutylammonium bromide, 1,2-dibromoethane (147 mL, 1.709 mol) was added slowly dropwise, with the rate of dropwise acceleration being controlled to maintain the temperature of the reaction at 50 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 50 °C for 1 hour. Upon completion of the reaction, the mixture was poured into cold water and extracted with diisopropyl ether. The organic phases were combined and the crude product was purified by high vacuum distillation to give 90 g of colorless liquid 1-phenylcyclopropane carbonitrile in 73% yield.
References
[1] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1775 - 1779
[2] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 10, p. 2086 - 2091
[3] Tetrahedron Letters, 2006, vol. 47, # 23, p. 3871 - 3874
[4] Patent: WO2011/61760, 2011, A1. Location in patent: Page/Page column 17-18
[5] Organic Letters, 2015, vol. 17, # 20, p. 4944 - 4947
