95741-44-9|5-(Benzyloxy)-2-bromo-1,3-dimethylbenzene| Ambeed

Yield	Reaction Conditions	Operation in experiment
60.2%		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). The reaction solution was stirred for 1.5 hours, added with tripropyl borate (5.64 g, 30 mmol), then heated to 30 C and stirred for 12 hours. The resulting solution was added dropwise with 10 mL of 2 M hydrochloric acid, then cooled down to the room temperature and stirred for another 2 hours. The resulting solution was concentrated under reduced pressure and filtere. 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 60.2%) as a white solid. MS m/z (ESI): 257.2 [M+1]
60%		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 -78C. The reaction mixture was stirred at the same temperature for 1.5 hr, and triisopropyl borate (20.9 mL, 90.6 mmol) was added. The mixture was allowed to warm to room temperature and stirred overnight. To the reaction mixture was added 2 M hydrochloric acid (150 mL) and the mixture was stirred for 2.5 hr. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. Cold hexane was added to the residue to allow crystallization. The precipitated crystals were collected by filtration, washed with cold hexane and dried to give the title compound (4.65 g, yield 60%) as colorless crystals. 1H NMR (CDCl3) delta: 2. 36 (6H, s), 4. 57 (2H, s), 5.04 (2H, s), 6.63 (2H, s), 7.28-7.47(5H, m).
1.38 g		Under argon 5-(benzyloxy)-2-bromo-1 ,3-dimethylbenzene (2,38 g) is dissolved in tetrahydrofuran (30 mL) and cooled to -78C. 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 (MgSO4). The solvents are evaporated and he residue is crystallized from n-hexane. The precipitate is filtered off and dried ti give the title compound. Yield: 1 .38 g; LC (method 7): tR = 0.94 min; Mass spectrum (ESI"): m/z = 255 [M-H]

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5-(Benzyloxy)-2-bromo-1,3-dimethylbenzene

CAS No.: 95741-44-9

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