2-BENZYLOXY-5-CHLOROPHENYLBORONIC ACID

Compound))) : (2-Benzyloxy-5-chlorophenyl)-boronic acid (WO 01/19814 A2) 2-Benzyloxy-5-chlorophenyl iodide (5g 0.0145 mol) in diethyl ether/tetrahydrofuran (100: 30) was cooled to-100°C. n-Butyl lithium, 1.6M solution in hexanes (10mL, 0.016 mol) was added dropwise over 15min under nitrogen. The reaction mixture was then allowed to rise to-70°C for 1 h. Triethylborate (9mL, 0.03 mol) was added dropwise under nitrogen. The cooling bath was then removed and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then quenched with 2N hydrochloric acid (40mL) and stirred vigorously at room temperature for 1 h. The product was then extracted with ethyl acetate, dried over magnesium sulphate and evaporated down to an oil. Purification was carried out on a Biotage (90g cartridge) with ether/iso-hexane (50: 50) to give the required product (wt; 2.8g i. e. 74percent yield).2- (Benzvloxv)-5-chloro-nhenvlboronic acid 2-(Benzyloxy)-5-chloro-iodobenzene (5g 0.0145 mol) in diethyl ether/tetrahydrofuran (100: 30) was cooled to-100°C. n-Butyl lithium, 1.6M solution in hexanes (10mL, 0.016 mol) was added dropwise over 15min under nitrogen. The reaction mixture was then allowed to rise to-70°C for 1 h. Triethylborate (9mL, 0.03 mol) was added dropwise under nitrogen. The cooling bath was then removed and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then quenched with 2N hydrochloric acid (40mL) and stirred vigorously at room temperature for 1 h. The product was then extracted with ethyl acetate, dried over magnesium sulphate and evaporated down to an oil. Purification was carried out on silica gel with diethyl ether/iso-hexane (50: 50) to give the title compound (2.8g, 74percent yield).Butyllithium (11. 5 ml, 28.7 mmol, 2.5 M) was added, under nitrogen, over 10 minutes, to a solution of 2-BENZYLOXY-5-CHLORO-IODOBENZENE (9 g, 26.2 MMOL) in THF (40 ML) AT-100°C. The reaction mixture was then warmed up AT-78°C and stirred for 1 hour (AT-78°C) before triisopropyl borate (18 ml, 78.4 MMOL) was added over 10 minutes. The reaction mixture was then warmed to room temperature before a solution of HCI (60 ml, 1 M) was added. The mixture was vigorously stirred for 1 1/2 hours. The organic phase was separated, washed sequentially with water and brine, dried (MGSO4) filtered and concentrated. The residue was triturated with a 30percent solution of ether in iso-hexane and filtered to give the title compound (3.62g, 53percent) as a white solid. 1H NMR (CDCI3) δ 5.12 (2H, s), 5.74 (2H, s), 6.91 (1H, d), 7.26 (1 H, s), 7, 35-7. 41 (5H, m), 7.81 (1 H, s).

suzuki reaction

Molecular Weight:262.50
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:262.0568021
Monoisotopic Mass:262.0568021
Topological Polar Surface Area:49.7
Heavy Atom Count:18
Complexity:246
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes