Dimethylformamide → Methyl 4-(3-bromophenyl)-2-oxobut-3-enoate

Participants

Reaction Conditions

Reaction Steps

4-(3-Bromo-phenyl)-2-oxo-3-butenoic acid potassium salt (41.0 g, 140.0 mmol) prepared in Step 1 and methyl iodide (15.0 mL, 238.0 mmol) were added to N,N-dimethylformamide (200.0 mL). The reaction mixture was stirred at 75° C. for 4 hours and then distilled water was added thereto. The reaction mixture was extracted with ethyl acetate. The extract was washed with a saturated solution of sodium hydrogen carbonate and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8) to give 10.0 g of the titled compound as a pale yellow solid.

Provenance & Evidence