Extended knowledge of 3650-78-0

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.

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. 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

820 mg (3.4 mmol) of methyl 4-bromocinnamate were dissolved in 7 ml of dry toluene, added with 116 mg (0.1 mmol) of Pd(PPh3J4, a solution of 374 mg (1.1 mmol) of 4- cyanobenzeneboronic acid in 2 ml of MeOH, 6.8 ml of 2M Na2CO3 in water, and refluxed 9 h. Addition of EtOAc, washing with water, then with brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures 9/1 gave 273 mg of methyl 3-(4-cyanobiphenylyl)acrylate, mp. 150-1520C.A solution of the above compound (270 mg, 1.02 mmol) and of 2-tetrahydropyranyl- O-hydroxylamine (117 mg, 1.02 mmol) in 14 ml THF was cooled at -780C, added with 1.07 ml of sodium hexamethyldisilazane, stirred 2 hrs, then heated at -2O0C, cooled again at – 780C, quenched with NH4CI, extracted with AcOEt, the extract evaporated and chromatographed (Merck silicagel) with Hexane/EtOAc 6/4 to give 189 mg of 2- EPO tetrahydropyranyloxyamide of 3-(4-cyanobiphenylyl)acrylic acid, as a white solid, mp. 211- 2130C.A solution of the above compound (187 mg, 0.54 mmol) in 5 ml of MeOH was treated with 30 mg (0.16 mmol) of p-toluenesulfonic acid, stirred 24 h at room temp, filtered and washed with MeOH, to give 96 mg of 3-(4-cyanobiphenylyl)acrylic acid hydroxyamide, mp. 212-2140C, Rf 0.3 (CH2CI2/MeOH 95/5), 1H NMR: (DMSO-d6): 6.54 (d, 1 H, -CH=, J = 15.3 Hz), 7.51 (d, 1 H, CH=, J = 15.3 Hz), 7.69 (d, 2H, 2Ar, J = 8.2 Hz), 7.82 (d, 2H, 2Ar, J = 8.2 Hz), 7.8-8.0 (m, 4H, 6Ar), 9.05 (s, 1 H, NH), 10.80 (s, 1 H, OH).

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:
Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; WO2007/383; (2007); A1;,
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