Boronic acid, (5-cyano-2-methoxyphenyl)- (9CI)

3-Bromo-4-methoxybenzonitrile (7.7 g, 36 mmol) and 481 triisopropyl borate (14 g, 73 mmol)were dissolved by adding 20 tetrahydrofuran (150 mL), and 2.5 mol/L 27 n-butyllithium (hexanesolution, 22 mL, 55 mmol) was slowly added over 20 min at −78° C. After stirring at −78° C. for 2 hr, to thereaction mixture was added 7percent 482 phosphoric acid (100 mL), and the mixture was heated to roomtemperature. The reaction mixture was partitioned, to the organic layer was added 12 dichloromethane, and the mixture was extracted with 5percent aqueous sodium hydroxide solution (200 mL). The aqueous layer waswashed with diethyl ether, adjusted to pH2.5 with 85percent phosphoric acid and the insoluble material wascollected by filtration. The obtained solid was washed with water, and dried to give the 483 titlecompound ( 5.1 g , 29 mmol, 79percent). MS (ESI) m/z 178 (M+H)+ 1H NMR (300 MHz, DMSO-d6) δ 8.03 (s, 2H), 7.86-7.78 (m, 2H), 7.13 (d, J=11.6 Hz, 1H), 3.85 (s, 3H).To 3-Bromo-4-methoxybenzonitrile (7.7 g, 36 mmol) and triisopropyl borate (14 g, 73 mmol) was added tetrahydrofuran (150 mL) for dissolution, and 2.5 mol/L n-butyllithium (hexane solution, 22 mL, 55 mmol) was gradually added over 20 min at - 78°C. After stirring at -78°C for 2 hr, 7percent phosphoric acid (100 mL) was added to the reaction mixture and the mixture was heated to room temperature. The reaction mixture was partitioned, dichloromethane was added to the organic layer, and the mixture was extracted with 5percent aqueous sodium hydroxide solution (200 mL). The aqueous layer was washed with diethyl ether, adjusted to pH 2.5 by adding 85percent phosphoric acid and insoluble material was collected by filtration. The obtained solid was washed with water and dried to give the title compound (5.1 g, 29 mmol, 79percent). MS (ESI) m/z 178 (M+H)To a 5-L, 3-neck flask fitted with an addition funnel and mechanical stirrer was added 3-bromo-4-methoxybenzonitrile (Lancaster; 159.0 g; 750 mmol), anhydrous THF (3.0 L), and triisopropylborate (345 mL; 282 g; 1.50 mol). The solution was cooled to-78 °C in a dry ice/acetone bath then a solution of 2.44 M n-butyllithium in hexane (461 mL; 1.12 mol) was added over a 20-minute period. After the addition was complete, the reaction mixture was stirred at-78 °C for 1 hour. The reaction mixture was quenched with 7percent aqueous phosphoric acid (2 L) and the reaction mixture was allowed to warm to room temperature. Stirring was stopped and the reaction mixture was allowed to stand overnight. The layers were separated, the aqueous phase discarded, and the organic phase was diluted with dichloromethane (2 L) and the organic phase was extracted with 5percent aqueous sodium hydroxide (2x1.7 L). The aqueous phase was washed with MTBE (1.5 L) then acidified to pH = 2.5 with 85percent aqueous phosphoric acid, resulting in the formation of a white precipitate. The precipitate was filtered and washed with water to give 2-methoxy-5-cyanophenylboronic acid (104 g, 78percent) as a white solid .

Molecular Weight:176.97
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:177.0597233
Monoisotopic Mass:177.0597233
Topological Polar Surface Area:73.5
Heavy Atom Count:13
Complexity:213
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes