2-Methoxy-5-methylphenylboronic acid

White solid

To the THF solution of 2-bromo-1-methoxy-4-methybenzene(1.39 g, 15 mmol) at -780° C. under nitrogen was added n-butyllithium (15 mmol) dropwise. After stiring at -78° C. for one hour, the solution was added to trimethylborate (15 mmol) in THF (100 mL). The reaction mixture was warmed to room temperature and continuously stirred for four hours before poured into 3N hydrochloride (125 mL), then extracted with ethyl acetate three time. The organics were combined, dried over magnesium and concentrated to give yellow-white solid(2.2 g, 89percent). 1H NMR (300 MHz, d6-DMSO) δ 7.6 (s, 1H), 7.38 (d, J=2.3 Hz, 1H), 7.19 (dd, J=8.4 Hz, 2.3 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 3.78 (s, 3H), 2.2 (s, 3H).2-Methoxy-5-methylphenylboronic Acid (Structure 37 of Scheme XI, where REXAMPLE 216 EXAMPLE 216 EXAMPLE 216 1, 2-Dihydro-2, 2, 4, 9-tetramethyl-5-coumarino[3, 4-f]quinoline (Compound 316, structure 41 of Scheme XI, where R1 =H, R2 =methyl) General procedure: A mixture of compound 67 4 (2mmol), boric acids or borates (2.4mmol), 68 [1, 1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5mol %), and 69 sodium carbonate (6mmol) in 11 1, 4-dioxane (8mL) and 56 water (4mL) was heated under nitrogen conditions (90C, 6h). After cooling to ambient temperature, the reaction mixture was filtered and concentrated. The residue was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane three additional times. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography to provide compounds 5a-q.

suzuki reaction

Molecular Weight:165.98
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:166.0801244
Monoisotopic Mass:166.0801244
Topological Polar Surface Area:49.7
Heavy Atom Count:12
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes