2-CHLORO-4-METHOXYNITROBENZENE

Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate, 36.3 mg of copper acetate, 12.5 mg of 2, 9-dimethyl-1, 10-o-phenanthroline, 39.4 mg of 2-nitro-5-methoxybenzoic acid and 17.5 mg of sodium chloride4 mL of dimethyl sulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction, Extraction with ethyl acetate 3 times, each time 10mL, The combined organic phases are concentrated, 25.1 mg of 2-nitro-5-methoxychlorobenzene was obtained, The yield is 67percent.(2) in a machine equipped with mechanical stirring, Drip funnel and reflux condenser in a 500m 1 three-necked flask, Add 98g concentration of 98percentOf 2, 4-dichloronitrobenzene and 200 g of anhydrous methanol, The 2, 4-dichloronitrobenzene was dissolved in a methanol solution, At room temperature, 95 g of 30percentOf sodium methoxide solution, 0.5 hours drop finished, The reaction was carried out at a reflux temperature of about 68 ° C for 5-6 hours, After the reaction, Methanol is distilled off at atmospheric pressure (can be recycled after methanol), Add water to salt, Stirring crystallization filtration, The product was recrystallized from 200 g of methanol (after steaming of the mother liquor, Methanol recycling), Filtered and dried to give 84.2 g2-chloro-4-methoxy nitrobenzene as pale yellow crystals, The measured content was 95.2percent and the yield was 85.5percent.To a solution of 2-chloro-4-fluoro-1-nitrobenzene (220 mg, 1.253 mmol) in THF(2 mL) was added sodium methoxide (7.52 mL, 0.5, 3.76 mmol). The mixture was stirredat room temperature for 1.0 h. LCMS indicated a completion of the reaction The mixture was diluted with EtOAc, quenched with saturated ammonium chloride. The organic layer was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. The crude product was purified with flash chromatography (loading inchloroform, 0percent to 30percent EtOAc in hexanes over 12 mm using a 12 g silica gel cartridge).The desired fractions were combined and concentrated to give Intermediate 93A (230 mg, 1.226 mmol, 98 percent yield) as a yellow liquid. ‘H NMR (400MHz, chloroform-d) 8.02 (d, J9.2 Hz, 1H), 7.03 (d, J2.6 Hz, 1H), 6.89 (dd, J=9.2, 2.6 Hz, 1H), 3.90 (s, 3H).LC-MS: method C, RT = 1.80 mm, MS (ESI) m/z: 188 (M+H)

Molecular Weight:187.58
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:187.0036207
Monoisotopic Mass:187.0036207
Topological Polar Surface Area:55
Heavy Atom Count:12
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes