3-BROMO-4-METHYL-5-NITROBENZOIC ACID METHYL ESTER

3-Bromo-4-methyl-5-nitrobenzoic acid (7.10 g, 27.3 mmol) and methanol (100 mL) were added to a 250 mL single-neck flask, then dichloro sulfoxide (2.96 mL, 41.0 mmol) was added dropwise at 0°C. The reaction mixture was stirred for 12 h at 90°C. The resulting mixture was concentrated in vacuo to remove the solvent. To the residue was added saturated sodium bicarbonate (200 mL) and the mixture was extracted with ethyl acetate (100 mL x 2). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo, then the residue was purified by silica gel chromatography (ethyl acetate/petroleum ether (v/v) = 1/30) to give the title compound as a pale yellow solid (6.36 g, 85percent).Thiolyl chloride (7.2g, 0.06mol) was added into methanol(50ml) drop-wisely at -5°C, and then followed by the addition of 3-bromo-4-methyl-5-nitrobenzoic acid(13g, 0.05mol). The reaction mixture was stirred for 30min at rt, and then refluxed for 2h. The mixtuer was evaporated at reduced pressure and the residue was purified by column chromatograph to give the product 3 (1 1.2g, 82percent).

Molecular Weight:274.07
XLogP3:2.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:272.96367
Monoisotopic Mass:272.96367
Topological Polar Surface Area:72.1
Heavy Atom Count:15
Complexity:265
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes