Synthetic Route of 630-18-2,Some common heterocyclic compound, 630-18-2, name is Pivalonitrile, molecular formula is C5H9N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 C. The obtained mixture was stirred for 30 min at 50 C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 C and the obtained mixture was stirred for 30 min in the temperature range of 50 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pivalonitrile, its application will become more common.
Reference:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts