2-BroMo-4-Methoxy-6-nitroaniline

To a solution of 4-methoxy-2-nitrobenzenamine (6.72 g, 40 mmol) in DCM (70 mL) at -20 C, bromine (2.50 mL, 48 mmol) was added dropwise. The mixture was stirred at -20 C for 30 min. The mixture was poured into ice-water. The pH was adjusted to 8 with saturated sodium bicarbonate aqueous solution and then extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM/petroleum ether = 1 :2) to yield the product (6.42 g, 65% yield). ESI-MS m/z: 247.0 [M +H]+.Reference Example 17 Synthesis of 2-bromo-4-methoxy-6-nitroaniline To a solution of 4-methoxy-2-nitroaniline (35 g) in dichloromethane (350 mL) was subsequently added dropwise bromine (12.9 mL) at -20 C. After stirring for 30 minutes at the same temperature, this was poured into ice water, adjusted to pH 7 to 8 with saturated sodium bicarbonate aqueous solution and then extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate). After concentration of the desired fraction, the resulting residue was crystallized from hexane and ethyl acetate and then collected by filtration to obtain the title compound as reddish orange crystals (29.6 g). NMR (CDCl3) delta [ppm]: 7.63 (1H, d, J=3 Hz), 7.44 (1H, d, J=3 Hz), 6.38 (2H, bs), 3.80 (3H, s)To a solution of t-Butyl nitrite (3.75 g, 36.4 mmol) and CuCl2 (3.92 g, 29.2 mmol) in acetonitrile (120 mL) at 60 C, was added 2-bromo-4-methoxy-6- nitrobenzenamine (6.0 g, 24.3 mmol) and the resulting mixture was stirred at 60 C overnight. The mixture was concentrated in vacuo. The residue was dissolved in DCM (100 mL), washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM/petroleum ether = 1 :3) to yield the product (5.01 g, 77% yield).

Molecular Weight:247.05
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:245.96400
Monoisotopic Mass:245.96400
Topological Polar Surface Area:81.1
Heavy Atom Count:13
Complexity:197
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes