1-BROMO-3,4-DIMETHOXY-2-METHYLBENZENE

To a solution of 1, 2-dimethoxy-3-methyl-benzene 9 (55 g, 361.8 mmol) in ACN (1.8 L) was added NBS (65.3 g, 369 mmol) portion wise and the mixture was stirred at rt for 24 h under nitrogen atmosphere. PREPARATIVE - . .??. . PREPARATION OF 3, 4-DIMETHOXY-2-METHYLPHENYL BORONIC ACIDTo a stirred solution of l-bromo-3, 4-dimethoxy-2-methoxy-3-methylbenzene (5 g, *2.6 rntnol) in 50 mL THF at -780C was added 1.6N ?-BuLi (16 mL, 26.0 mmo) drop wise. After addition, the solution was allowed to stir at -780C for lOmin. Then, triisopropylborate (6 mL, 26.0 mmol) was added and the mixture was stirred further for 30m in. 2N HCl (5OmL) was added to the reaction mixture and it was stirred at ambient temperature for 4h. The reaction mixture was partitioned between saturated NaHCtheta3 and EtOAc, the layers were separated, and the aqueous layer was extracted again with EtOAc. The combined organic layers were dried (MgSO, ?), filtered, and evaporated in vacuo. The resulting material was purified by silica gel chromatography (40% EtOAc in hexane) to provide the product. 1H NMR (500 MHz, CDCl3) delta (ppm): 8.04 (d, IH), 6.95 (d, IH), 4.00 (s, 3H), 3.86 (s, 3H), 2.80 (s, 3H).A solution of 1-bromo-3, 4-dimethoxy-2-methyl-benzene 10 (4.8 g, 20.86 mmol), NBS (3.7 g, 20.89 mmol) and AIBN (680 mg) in ethyl acetate (265 ml) was heated overnight at reflux. After filtration and evaporation of the solvent, the residue was dissolved in CH2Cl2, washed with sat. aq NaHCO3, water, dried over Na2SO4, and evaporated in vacuum to afford white solid (4.7 g, 73.4%) which was pure enough for further use. 1H NMR (CDCl3, 400 MHz) delta 7.26 (d, J = 9.4 Hz, 1H), 6.76 (d, J = 8.8 Hz, 1H), 4.69 (s, 2H), 3.96 (s, 3H), 3.84 (s, 3H); 13C NMR (CDCl3, 100 MHz): delta 152.2, 148.6, 131.5, 127.9, 115.2, 113.8, 61.0, 55.9, 28.0; GC-MS (EI) 310 m/z [M+].

Molecular Weight:231.09
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:229.99424
Monoisotopic Mass:229.99424
Topological Polar Surface Area:18.5
Heavy Atom Count:12
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes