(4-METHYL-1-NAPHTHALENE)BORONIC ACID

Off-white powder

3.4. 4-Methyl-1-naphthylboronic acid 4 A solution of n-BuLi (1.7 M in hexane, 10 mL) was slowly added to a cooled (-78 °C) solution of 1-bromo-4-methyl naphthalene (1.5 g, 6.78 mmol) in dry ether (200 mL). The mixture was then allowed to warm up and stirred at room temperature for 2 h. It was then cooled back (-78 °C) and a solution of tri-iso-propyl borate (4 g, 4.91 mL, 21.27 mmol) in ether (20 mL) was rapidly added. The mixture was stirred at -78 °C for 30 min and then at room temperature for 15 h. Then, 100 mL of HCl (2 M) was added and milky white emulsion gradually became clear. The ethereal layer was then separated and the aqueous layer was extracted with ether (3≍100 mL). The combined ether solutions were dried (MgSOIn a 100 ml three-necked flask, compound 4''' (10 mmol, 2.48 g) and THF (50 ml) were added, and n-butyllithium (11 mmol, 1.6 M, 6.88 ml) was slowly added dropwise under nitrogen atmosphere at -78°C. The reaction was carried out at -78°C for 2 hours, and then 5 ml of a THF solution of triisopropyl borate (15 mmol, 3.03 g) was slowly added dropwise to the reaction system. After the addition was completed, the mixture was slowly warmed to room temperature and stirred overnight. After the disappearance of the TLC test material, the reaction was completed. reaction. The mixture was quenched with dilute hydrochloric acid (20percent, 20 ml), stirred at room temperature for 3 hours, then extracted with ethyl acetate (50 ml*3), and the combined organic phases were washed with saturated brine (100 ml*3) and dried over anhydrous sodium sulfate. The organic phase was concentrated and purified by column chromatography to give compound 3''' (7.8 mmol, 1.45 g, 78percent).

Molecular Weight:186.02
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:186.0852098
Monoisotopic Mass:186.0852098
Topological Polar Surface Area:40.5
Heavy Atom Count:14
Complexity:196
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes