Uses
An intermediate in the production of protein A mimetics, serotonin antagonists, and other CNS agents
Synthesis
Preparative Example 1 Synthesis of 4-fluorophenethyl bromide: Triphenylphosphine (222 g) and N-bromosuccinimide (151 g) were sequentially added to a solution of 4-fluorophenylethanol (100 g) in dichloromethane (1 L) under cooling conditions in an ice bath and the reaction was carried out with continuous stirring for 1 hour. Upon completion of the reaction, the resulting solution was concentrated under reduced pressure and the precipitated crystals were subsequently filtered. The filtrate was further concentrated to afford the target product 4-fluorobromoethylbenzene (133 g) as a colorless oil (yield: 92%). The product was characterized by 1H-NMR (400 MHz, CDCl3): δ (ppm) 3.14 (2H, t, J = 8 Hz), 3.54 (2H, t, J = 8 Hz), 6.98-7.03 (2H, m), 7.15-7.18 (2H, m).
References
[1] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 7035 - 7044
[2] Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 585 - 596
[3] Patent: US2002/19531, 2002, A1
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 2989 - 3002
[5] Patent: EP2508526, 2012, A1. Location in patent: Page/Page column 48
