(3-Cyanophenyl)boronic acid pinacol ester

White solid

To a stined solution of 3-amino-benzonitrile (0.5 g, 4.23 mmol) in acetonitrile (30 mL) is added tert-butylnitrite (0.7 mL, 6.34 mmol) and bispinacolatodiboron (1.29 g, 5.076 mmol) at 0 °C. The mixture is heated at 80 °C for 2 hours. The reaction mixture iscooled to room temperature and concentrated under reduced pressure. The crude material is purified by silica gel column chromatography (combiflash) eluting in 4percent EtOAc/hexanes to obtain the title compound (0.35 g, 99.8percent). LCMS m/z 294 (M+H)+To a stirred solution of 3-amino-benzonitrile (0.5 g, 4.23 mmol) in acetonitrile (30 mL) is added tert-butylnitrite (0.7 mL, 6.34 mmol) and bispinacolatodiboron (1.29 g, 5.076 mmol) at 0° C. To a solution of 3-cyanophenyl boronic acid (2.5 g, CAS: 150255-96-2) in anhydrous THF (150 ml) under an atmosphere of nitrogen were added pinacol (2.95 g) and Na2SO4 (10 g) at 25°C.The reaction mixture was stirred for 12 h at 25°C under an atmosphere of nitrogen. Then, Na2SO4was filtered off and all volatiles were evaporated. The residue was partitioned between ethylacetate and water. The organic layer was then separated, dried over Na2SO4 and concentrated to afford the title compound (4.72 g) as off white solid which was directly used in the next reaction step without further characterization.

Molecular Weight:229.08
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:229.1274089
Monoisotopic Mass:229.1274089
Topological Polar Surface Area:42.2
Heavy Atom Count:17
Complexity:329
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes