[2,6-Dimethyl-4-(phenylmethoxy)phenyl]boronic acid

5-(Benzyloxy)-2-bromo-1, 3-dimethylbenzene 12a (2.91 g, 10 mmol, prepared by a method disclosed in patent application ) was dissolved in 35 mL of tetrahydrofuran in an dry-ice bath, followed by addition of n-butyllithium (4.8 mL, 12 mmol). To a solution (100 mL) of 5-(benzyloxy)-2-bromo-1, 3-dimethylbenzene (8.78 g, 30.2 mmol) in tetrahydrofuran was added n-butyllithium hexane solution (1.6 M, 22.6 mL, 36.2 mmol) under stirring at -78°C. Under argon 5-(benzyloxy)-2-bromo-1 , 3-dimethylbenzene (2, 38 g) is dissolved in tetrahydrofuran (30 mL) and cooled to -78°C. n-Butyllithium (6.2 mL of a 1 .6 M solution in tetrahydrofuran) is added dropwise, the mixture is stirred for 4 hours followed by dropwise addition of triisopropyl borate (5.7 mL). The mixture is stirred for 12 hours while warming to room temperature. Then the mixture is poured on 2 N hydrochloric acid and stirred vigorously for 30 minutes. The phases are separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with brine and dried (MgSOS-(Benzyloxy)-2-bromo-1, 3-dimethylbenzene 12a (2.91 g, 10 mmol, prepared by a method disclosed in PCT patent application WO2005019151) was dissolved in 35 mL of tetrahydrofuran in a dry-ice bath, followed by addition of n-butyllithium (4.8 mL, 12 mmol). The reaction solution was stirred for 1.5 hours, mixed with tripropyl borate (5.64 g, 30 mmol), then heated to 30° C. and stirred for 12 hours. To the resulting solution, 10 mL of 2M hydrochloric acid was added dropwise, then the solution was cooled down to room temperature and stirred for another 2 hours. The resulting solution was concentrated under reduced pressure and filtered. The filter cake was washed with water (10 mL) and n-hexane (10 mL) successively to obtain the title compound (4-(benzyloxy)-2, 6-dimethylphenyl)boronic acid 12b (1.54 g, yield 60.2percent) as a white solid. MS m/z (ESI): 257.2 [M+1]

Molecular Weight:256.11
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:256.1270746
Monoisotopic Mass:256.1270746
Topological Polar Surface Area:49.7
Heavy Atom Count:19
Complexity:254
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes