Reference of 2905-65-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
NaHMDS (2M, 5.50 mL) was added to a solution of pent-4-enenitrile (0.97 mL, 10.0 mmol) in anhydrous THF (50 mL) at -78 oC. After stirring for 15 min, methyl-3-chlorobenzoate (1.88 g) was added and the reaction was stirred for 30 min befor warming to room temperature. The reaction was quenched by addition of 1N HCl solution, then extracted with EtOAc (x 2). The combined organics were dried and concentrated to give the acylated nitrile (2.18 g, 99%). Hydroxylamine hydrochloride (382 mg) was added to a solution of the acylated nitrile (1.1 g) in pyridine (10 mL) and the reaction was stirred at 80 oC for 3 hours. After cooling to room temperature, EtOAc and sat. NH4Cl solution were added and the layers separated. The organic was washed with brine, dried over Na2SO4 and concentrated to give the amino-isoxazole as a yellow oil (1.05 g, 89%) which was used directly. The residue was dissolved in pyridine (5 mL) and cooled in an ice-bath. AcCl (0.36 g, 4.5 mmol) was added and the reaction was stirred for 30 min before warming to room temperature for a further 30 min. The volatiles were removed under vacuum and the residue was purified by silica gel chromatography [heptane/EtOAc, 9:1 – 3:1] to give the product as a colourless oil (0.96 g, 77%). The N-acyl intermediate (950 mg, 3.43 mmol) was then N-alkylated with allyl bromide and NaH to give the product 19 as a colourless oil (855 mg, 79%)
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 3-chlorobenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Moss, Thomas A.; Tetrahedron Letters; vol. 54; 8; (2013); p. 993 – 997;,
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