Reference of 906673-45-8,Some common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
40.0 g (131 mmol) of 4-(4-bromo-3-hydroxymethyl-phenoxy)-benzonitrile of formula (II), prepared as described in Example 3, are added under nitrogen to 400 mL THF and 23.8 g (236 mmol) of triethylamine in a previously anhydrified flask. The solution is cooled down to 0 C. and 16.9 g (157 mmol) of trimethylsilyl chloride are added maintaining the temperature below 15 C. After completion of the addition, the mixture is allowed to reach room temperature. 50 mL of toluene and 100 mL of water are added and the phases are separated. The organic phase is washed with a saturated NaCl solution and evaporated to dryness under reduced pressure to obtain 49.4 g of 4-(4-bromo-3-trimethylsilanoxymethyl)-benzonitrile of formula (II) as a solid with a yield of 98%. The obtained product is used in the next step any without further purification. 1H-NMR (CDCl3, 300 MHz) delta (ppm): 7.63-7.60 (2H, m) 7.52 (1H, d, J=8.4 Hz), 7.22 (1H, m) 7.03-7.00 (2H), 6.85-6.80 (1H, m) 4.69 (2H, s), 0.17 (9H, s)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, its application will become more common.
Reference:
Patent; DIPHARMA FRANCIS S.R.L.; Santillo, Niccolo’; Attolino, Emanuele; Brenna, Davide; Vladiskovic, Chiara; Lombardo, Alessandro; Razzetti, Gabriele; US2019/241585; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts