Methyl 3-(ChloroMethyl)-5-nitrobenzoate synthesis

Yield:142320-39-6 92%

Reaction Conditions:

with thionyl chloride in dichloromethane;Heating / reflux;

Steps:

3-Chloromethyl-5-nitro-benzoic acid methyl ester (CAB04081):; Thionyl chloride (5 ml) was added to a solution of CAB04080 (4.223,20.0 mmol) in DCM. The dark solution was heated to reflux until the production gas ceased (ca. 30 min) and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc/hexane 1 : 5, Rf: 0.45) to give the title compound as a light yellow solid. Yield: 4.225 g (92%). 1H-NMR(400 MHz, CDCl3) 8 4.03 (3H, s, -OCH3), 4.73 (2H, s, -CH2CI), 8.43 (1H, m), 8.49 (1H, dd, J = 2.0, 2.0 Hz), 8.85 (1H, dd, J = 2.0, 2.0 Hz) ; 1³ C-NMR (100.5 MHz, CDC13) No. 44.1,53.0 (OCH3), 124.4,127.3, 132.4,135.1 140.6, 164.5 (one carbon not resolved); MS (FAB+): m/z 229.9 (100%, [C9H8ClNO4]+); HPLC (ACS80) tr = 2.199 min (>99%).

References:

WO2005/118560,2005,A1 Location in patent:Page/Page column 70