5-Bromo-2-hydroxybenzamide

A. 5-bromo-2-hydroxybenzamide; 0 OH 0 OH 1. n-butanol, H2SO4, reflux HO X 2. NH3, MeOH H2N 82percent Br Br To a stirred solution of 5-Bromosalicyclic acid (30 g, 135.5 mmol) in n-butylalcohol (60 mL) was added H2SO4 (95.6percent, 289 L, 5.42 mmol) in a 100 ml round bottom flask connected by a Dean-Stark trap/reflux condenser that was filled with 12 ml of n-butylalcohol. After heated to reflux for 2 days, the reaction was cooled down to R. T. and concentrated to give a pale yellow oil. The mixture was added 50 mL MeOH, followed by NH3 in MeOH (7 N, 116 mL). The reaction was stirred at R. T. for another 2 days, monitored by HPLC. After the reaction complete, it was concentrated to give a white solid. The crude solid was washed with small amount of EtOAc and hexane to afford 24 g of the product as a white crystalline solid (82percent yield).A solution of 5-bromo-2-hydroxybenzoic acid (20 g, 92.16 mmol, 1.00 equiv) in thionyl chloride (50 mE) was stirred at 80° C. for 4 h. The mixture was concentrated under vacuum. Then the residue was added to a solution of ammonia (50 mE) in tetrahydrofuran (50 mE) and stirred at room temperature for 2 h. Ethyl acetate (50 mE) was added to the reaction. The solid was filtered out. The filtrate was concentrated under vacuum and purified by Si02 chromatography eluted with ethyl acetate/petroleum ether (1:5) to afford 4.5 g (23percent) of 5-bromo-2-hydroxybenzamide as a yellow solid. EC-MS: mlz=216 [M+H].In a 100 mL round bottom flask, 1.5 g (0.011 mol) of salicylamide was stirred and dissolved in 21.9 mL of glacial acetic acid.0.556 mL (0.011 mol) of liquid bromine in glacial acetic acid solution was slowly added dropwise at room temperature, the reaction was stirred, and the reaction was traced to the end point by TLC.The product was poured into cold water to precipitate a large amount of white solid.After suction filtration, the vacuum drying oven was dried at 50 ° C to obtain 1.85 g of a white powdery solid.Melting point: 211-212 ° C, yield 78percent.In a 100 mL round bottom flask, 1.5 g (0.011 mol) of salicylamide was stirred and dissolved in 21.9 mL of glacial acetic acid.0.556 mL (0.011 mol) of liquid bromine in glacial acetic acid solution was slowly added dropwise at room temperature, the reaction was stirred, and the reaction was traced to the end point by TLC.The product was poured into cold water to precipitate a large amount of white solid.After suction filtration, the vacuum drying oven was dried at 50 C to obtain 1.85 g of a white powdery solid.Melting point: 211-212 C, yield 78%.

Molecular Weight:216.03
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:214.95819
Monoisotopic Mass:214.95819
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes