In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37924-85-9,3-(Bromomethyl)benzo[d]isoxazole, as follows.37924-85-9
General procedure: To NaOMe (25% soln, 0.5 mL, 2.2 mmol) in MeOH (5 mL) was added thiosemicarbazide 9 (200 mg, 2.2 mmol). Diethyloxalate (0.3 mL, 2.2 mmol) was then added dropwise. The mixture was heated at 65 C for 2 h and then cooled to rt. 1-(Bromomethyl)-4-chlorobenzene (500 mg, 2.4 mmol) was added in one portion; stirring was continued at rt for 3 h and then heated overnight at 50 C. The reaction mixture was concentrated. The residue was dissolved in EtOAc (40 mL), washed with water (20 mL), and brine (20 mL). The organic phase was dried over Na2SO4, concentrated and purified by silica gel column chromatography (EtOAc w/ 0.2% HOAc). The product was triturated in Et2O to afford 59 mg of 6g as a light yellow solid (10% yield)
According to the analysis of related databases, 3-(Bromomethyl)benzo[d]isoxazole, the application of this compound in the production field has become more and more popular.
Reference£º
Article; Hin, Niyada; Duvall, Bridget; Berry, James F.; Ferraris, Dana V.; Rais, Rana; Alt, Jesse; Rojas, Camilo; Slusher, Barbara S.; Tsukamoto, Takashi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2088 – 2091;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics