BENZENEMETHANOL, 2-BROMO-6-NITRO-

To a solution of acetic acid 2-bromo-6-nitro-benzyl ester (536 mg, 1.96 mmol) in water (20 rnl) was added KOH solution (10percent, 1.5 ml). The reaction was heated under reflux overnight. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate. The combined extracts were treated with MgS04, and concentrated under vacuum to give (2-bromo-6-nitro-phenyl) -methanol (389mg, 86percent) as a yellow solid. 1H NMR (CDC13, 300MHz) 8 : 4.93 (d, J = 7.43Hz), 7.354 (t, J = 8. 10Hz), 7. 84 (dd, J = 1.23Hz, 8. 17Hz), 7.89 (dd, J = 1.22Hz, 8.03Hz).EXAMPLE 512-amino-6-bromobenzyl alcohol (intermediate I-1)2-nitro-6-bromo-toluene (32.20 g, 0.20 mol), N-bromosuccinimide (26.6 g, 0.20 mol), and benzoyl peroxide (0.40 g, 2 mmol) were dissolved in chlorobenzene (100 ml), and heated to reflux for about 20 h. The reaction was stopped, and the reaction mixture was filtered to obtain a filtrate. The filtrate was concentrated under vacuum to obtain a light brown oily product, which was recrystallized with ethanol to obtain a yellow solid 2-nitro-6-bromo benzyl bromide (47.31 g, 81percent).2-nitro-6-bromo benzyl bromide (14.70 g, 0.05 mol) and anhydrous sodium acetate(14.7 g, 0.15 mol) were added into N, N-dimethylformamide (70 ml), heated and reacted for about 1 h at 70° C., and cooled to room temperature. The reaction mixture was added into water (150 ml), extracted with ethyl acetate three times, washed with water three times, washed with saturated sodium chloride solution three times, dried by anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum to obtain a white solid 2-nitro-6-bromo phenyl acetic acid methyl ester (12.65 g, 92percent).2-nitro-6-bromo phenyl acetic acid methyl ester (2.73 g, 0.01 mol) was added into the water (100 ml), and 10percent potassium hydroxide solution (20 ml) was added dropwise. The reaction mixture was heated to reflux for 2 h, cooled to room temperature, and extracted with ethyl acetate for three times. The organic phase was combined, washed with water and with saturated sodium chloride solution sequentially, dried by anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum to obtain a yellow solid 2-bromo-6-nitro-benzyl alcohol (1.91 g, 83percent).2-bromo-6-nitro methanol (1.15 g, 5 mmol), sodium sulfide (0.78 g, 10 mmol), and sulfur (0.32 g, 10 mmol) were dissolved in ethanol (50 ml) and water (25 ml), heated to reflux for 2 h, and then cooled to room temperature. The ethanol was evaporated by concentration under vacuum, and the rest of the reaction mixture was added into water (30 ml), and extracted with ether three times. The organic phase was combined, washed with water and with saturated sodium chloride solution sequentially, dried by anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum to obtain a yellow solid 2-bromo-6-amino-benzyl alcohol (0.78 g, 78percent), [M+H]2-nitro-6-bromo phenyl acetic acid methyl ester (2.73 g, 0.01 mol) was added into the water (100 ml), and 10percent potassium hydroxide solution (20 ml) was added dropwise. Will be loaded with 2-bromo-6-nitrobenzyl acetate(12.0 g, 43.8 mmol), aqueous sodium hydroxide (3M, 50 mL)The mixed solution with 50 mL of ethanol was stirred at room temperature overnight.After TLC showed that the reaction of the starting material was complete, the reaction was diluted with water and extracted with EA (50 mL×3).The organic phase is backwashed with saturated brine and dried over anhydrous Na2SO4.9.5 g after evaporation in vacuoTarget compound, yellow solid

Molecular Weight:232.03
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:230.95311
Monoisotopic Mass:230.95311
Topological Polar Surface Area:66
Heavy Atom Count:12
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes