Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-5-fluorobenzonitrile
General procedure: To a solution of 5 (500 mg, 2.55 mmol) in 10 mL of DMF was successively added Et3N (1.42 mL, 10.2mmol), 9a (579 mg, 2.55 mmol), CuI (48 mg, 0.25 mmol), and trans-dichlorobis(triphenylphosphine)palladium (177 mg, 0.25 mmol). The resulting solution was warmed to 60 oC, and TBAF 1M in THF (2.8 ml, 2.80mmol) was added dropwise. After 2h at this temperature the mixture was hydrolyzed with 50 mL of H2O and, extracted with AcOEt (4 X 30 mL). The organic layer was washed with saturated NaCl (3 X 30 mL), dry over anhydrous Na2SO4, and concentrated on a rotary evaporator. Purification of the residue by column chromatography (hexane/AcOEt 8/2) yielded 439 mg (64 %) of 1a as an off white solid. 1H NMR (CDCl3), d = 2.67 (s, 3H, CH3); 7.46 (s, 1H, CHAr); 8.00 (t, 1H, J= 1.6 Hz, CHAr); 8.35 (t, 1H, J=1.6 Hz, CHAr); 8.47 (t, 1H, J=1.6 Hz, CHAr). 13C NMR (CDCl3), d = 19.6 (1C, CH3); 84.6 (1C, C?C); 89.1 (1C, C?C); 114.8 (1C, Cq); 116.3 (1C, Cq); 125.5 (1C, CHAr); 126.5 (1C, CHAr); 126.6 (1C, CHAr); 130.4 (1C, CHAr); 135.4 (1C, Cq); 140.1 (1C, CHAr); 148.6 (1C, Cq); 166.9 (1C, Cq). Anal (C13H7N3O2S, HCl) C, H, N.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
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