Hydrochloric Acid → HCID 11429986, compound

Participants

Reaction Steps

Dimethyl oxalate (127.79 g, 5.0 eq) was added to sodium methylate (216.4 mL, 28%, 5.0 eq). The resulting mixture was stirred at room temperature for 1.5 hours. To the mixture was then added 5-iodo-2-methyl-3-nitrobenzotrifluoride (71.64 g, 216.4 mmol), dissolved in MeOH (216 mL). The dark red mixture was then stirred at room temperature for 6 hours and left over night. The solvent was removed in vacuo to give a red solid which was subsequently added to aqueous 2.5N HCl (800 mL). The mixture was extracted with EtOAc (500 mL and 2×300 mL). The extracts were combined and dried (anhydrous MgSO4). After filtration, the solvent was removed in vacuo to give a yellow solid of the crude product (161.41 g). A fraction of this was purified by column chromatography (silica gel, eluting 15:1 to 10:1 hexane:EtOAc) to give the title compound as a yellow solid.

Provenance & Evidence