2-(1,3,2-Dioxaborinan-2-yl)benzonitrile

3.69 g (48.5 mmol) of 1, 3-propanediol was added to the organic phase obtained in Example 1, and the mixture was stirred at room temperature for 1 hour. After separation of the separated aqueous phase, the solvent was distilled off with an evaporator. 2 ml of toluene and 120 ml of heptane were added to the remaining oily matter to precipitate crystals. The obtained crystals were washed with 30 ml of heptane and then dried, 7.44 g (yield: 82.4percent) of 1, 3-propanediol ester (2- (1, 3, 2-dioxaborinan-2-yl) benzonitrile) of 2-cyanophenylboronic acid was obtained. The crystal contained 0.40percent of 1-phenyl-1- (2, 2, 6, 6-tetramethylpiperidin-1-yl) methylimineStep 1: Synthesis of 2-(1, 3, 2-dioxaborinan-2-yl)benzonitrile Step 1: synthesis of 2-(1, 3, 2-dioxaborainan-2-yl)benzonitrile 49.0 g (334 mmol) 2-cyano-benzeneboronic acid and 25.9 g (340 mmol) 1, 3-propanediol and stirred while 2 ℓ 1 ℓ round bottom flask in CH2Cl2 20 hours dongan was dissolved. Then, the solution was poured into a suction filter to remove the solids on the gum. Then, the filtrate was dried over anhydrous MgSO4 and removal of the residue, filtered, to give a lighter colored oil by evaporation of the solvent. Thereafter, the oil was dissolved in CH2Cl2, was purified using CH2Cl2 as eluent on a silica gel plug. Distilling the product fractions to obtain the product (35.7 g, 57.2percent yield) as a clear oil2-cyano phenyl boronic acid and 1, 3 propanediol was solubilized in anhydrous toluene. The reaction mixture was refluxed in a flask equipped with a Dean-Stark apparatus. After 24 h, the reaction was concentrated under reduced pressure to give colorless oil. The crude product was purified on silica gel (DCM) to give 2-[1-3]dioxaborinan-2-yl-benzonitrile; yield: 20percent;

Molecular Weight:187.00
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:187.0804587
Monoisotopic Mass:187.0804587
Topological Polar Surface Area:42.2
Heavy Atom Count:14
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes