Methyl 2-(4-fluoro-2-nitrophenyl)acetate synthesis

Yield:147124-38-7 54%

Reaction Conditions:

with water;lithium chloride in dimethyl sulfoxide at 100; for 21 h;

Steps:

118

Dimethyl (4-fluoro-2-nitrophenyl)malonate (5.0 g, 18 mmol), lithium chloride (1.6 g, 38 mmol) and water (0.33 g, 18 mmol) were combined in dimethyl sulfoxide (100 mL) and heated at 100° C. After 21 hours, the cooled solution was poured into a stirred mixture of saturated brine (200 mL) and ethyl acetate (200 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (200 mL). The combined organic extracts were washed with saturated brine (2*200 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a dark oil (4.0 g) that was dissolved in dichloromethane and pre-adsorbed on silica gel (10 g). Flash column chromatography (silica 190 g, 5%, 10%, 20% ethyl acetate/hexanes) provided methyl (4-fluoro-2-nitrophenyl)acetate (2.1 g, 54%) as a yellow oil. MS (ES) m/z 212 [(M-H)^-].

References:

US2007/72897,2007,A1 Location in patent:Page/Page column 85