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. 70591-86-5, name is 3-Bromobenzoylacetonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H6BrNO
General procedure: To a solution of catalyst 4 (0.01mmol), 3,5-(NO2)2C6H3CO2H (0.02mmol), and alpha,beta-unsaturated aldehyde 2 (0.10mmol) in toluene (1.0mL) was added alpha-cyanoketones 1 (0.15mmol) at 0C. The resulting solution was then stirred for 48h. After complete consumption of the aldehyde (as monitored by TLC), the reaction mixture was evaporated and then loaded onto silica gel (ethyl acetate/petroleumether=1:10 to 1:7) and the products 3a-n were obtained by column chromatography. The title compound was obtained according to the general procedure (85% yield) as a mixture of two diastereoisomers (major and minor). Yellow solid; [alpha]D30=+31.3 (c 1.60, CHCl3); mp=170-172C; 1H NMR (400MHz, CDCl3): delta 7.89 (s, 1H; minor), 7.87 (s, 1H; major), 7.79 (d, J=8Hz, 1H; both diastereoisomers), 7.59 (d, J=8Hz, 1H; both diastereoisomers), 7.41-7.37 (m, 2H; both diastereoisomers), 7.33-7.28 (m, 4H; both diastereoisomers), 5.66-5.63 (m, 1H; major), 5.60-5.56 (m, 1H; minor), 3.95 (dd, J=9.6, 6.4Hz, 1H; major), 3.90 (dd, J=10.0, 6.4Hz, 1H; minor), 3.57 (d, J=4Hz, 1H; major), 3.54 (d, J=7.2Hz, 1H; minor), 2.52-2.46 (m, 1H; minor), 2.30-2.24 (m, 1H; major), 2.09-2.03 (m, 1H, both diastereoisomers); 13C NMR (100MHz, DMSO-d6): delta 162.0, 142.2, 141.9, 136.2, 133.8, 131.1, 131.0, 129.2, 128.4, 128.1, 127.7, 127.6, 121.9, 119.6, 97.4, 93.3, 88.5, 36.6, 35.9ppm; (additional peaks are observed due to diastereoisomers). IR (KBr): nu 3386.4, 2207.0, 1607.8, 1591.1, 1559.7, 1473.7, 1148.5, 1100.6, 1073.6, 950.9, 861.8, 829.0, 791.0, 765.5cm-1; d.r.: trans/cis=3.79/1; ESI-MS (m/z): 354.1 (M-H)-; HRMS(ESI): calcd for ([C18H14NO2BrNa+]): 378.0100. Found: 378.0100; enantiomeric excess: 92%, determined by HPLC (Chiralcel OD-H column, hexane/ i-PrOH 80:20, flow rate 0.7mL/min; lambda=254nm, tmajor=18.5min, tminor=11.2min).
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.