Synthesis
Methyl 3-(cyanomethyl)benzoate is synthesised using Methyl 3-(bromomethyl)benzoate as raw material by chemical reaction. The specific synthesis steps are as follows:
(i) To a solution of methyl 3-bromobenzoate (10.0 g, 44 mmol) in acetonitrile (100 mL) were added potassium cyanide (5.7 g, 87 mmol) and 18-crown-6 (1.0 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95-->30/70), and the fraction containing the object product was concentrated under reduced pressure to give the title compound (7.0 g, 91percent) as a colorless oil. 1H-NMR (DMSO-d6, 300 MHz) δ 3.88 (3H, s), 4.17 (2H, s), 7.57 (1H, t, J = 7.6 Hz), 7.61 - 7.69 (1H, m), 7.88 - 7.95 (1H, m), 7.97 (1H, br s).
References
[1] Patent: WO2006/67446, 2006, A1. Location in patent: Page/Page column 126
[2] Patent: WO2006/79791, 2006, A1. Location in patent: Page/Page column 34
[3] Patent: WO2006/24834, 2006, A1. Location in patent: Page/Page column 63-64
[4] Patent: WO2006/24836, 2006, A1. Location in patent: Page/Page column 27
[5] Patent: WO2007/71955, 2007, A1. Location in patent: Page/Page column 50-51
