Some common heterocyclic compound, 1194-02-1, name is 4-Fluorobenzonitrile, molecular formula is C7H4FN, 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. Formula: C7H4FN
27.1 g (197 mmol) of K2CO3, 12.13 g (100.3 mmol) of 4-fluorobenzonitrile of formula (IV), 34.2 g (98.3 mmol) of 1-bromo-4-trimethylsilanoxy-2-trimethylsilanoxymethyl benzene of formula (III), obtained as described in Example 2, and 60 mL of DMSO are placed under nitrogen in a previously anhydrified flask. The reaction mixture is heated to 105 C. and kept at the same temperature for 2 hours. Then, 120 mL of toluene and 240 mL of H2O are added, the phases are separated and the organic phase is washed with a solution of 10% K2CO3. The organic phase is allowed to cool down to room temperature and the product is allowed to crystallize providing 19.7 g 4-(4-bromo-3-hydroxymethyl-phenoxy)-benzonitrile of formula (II) with a yield of 66%. 1H-NMR (DMSO-d6, 300 MHz) delta (ppm): 7.85-7.80 (2H, m) 7.62 (1H, d, J=8.4 Hz), 7.22 (1H, d, J=3.0 Hz), 7.13-7.11 (2H, m) 6.98 (1H, dd, J=3.0, J=8.4 Hz), 4.47 (2H, s)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1194-02-1, 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