Reference of 5905-69-1,Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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.
Step 3. Synthesis of ethyl 5-(4-(difluoromethoxy)phenyl)isoxazole-3- carboxylate [1.2.11c] 1.2.11c A vial was charged with 1.2.11 b (0.76 g, 1.77 mmol, 1.0 equiv) and 1-bromo-4- uoromethoxy) benzene (0.5 g, 2.13 mmol, 1.2 equiv) were dissolved in 1 ,4-dioxane (10 ml_). Pd(PPh3)2CI2 (0.062 g, 0.085 mmol, 0.05 equiv) was added and the reaction mixture was stirred at 130 C for 2 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (0-10 % EtOAc in Hexane) to afford product 1.2.11c (0.6 g, 94 % yield). LCMS (m/z): 284.2 [M+H]. 1H NMR (400 MHz, CDCI3) delta 7.89 – 7.81 (m, 2H), 7.28 – 7.24 (m, 2H), 6.93 (s, 1 H), 6.4 – 6.9 (3s, 1 H), 4.19 (q, J = 7.1 Hz, 2H), 1.31 – 1.29 (t, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-(difluoromethoxy)benzene, its application will become more common.
Reference:
Patent; NOVARTIS AG; FU, Jiping; KARUR, Subramanian; MADERA, Ann Marie; PECCHI, Sabina; SWEENEY, Zachary Kevin; TJANDRA, Meiliana; YIFRU, Aregahegn; WO2014/160649; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem