Iodoethane → HCID 58424902, compound

Participants

Reaction Steps

3-Methoxy-5-nitrobenzoic acid (10 g, 50.7 mmol) prepared in step 1 of Example 72 was dissolved in dichloromethane (200 ml), added with 1 M boron tribromide dichloromethane solution. The reaction mixture was stirred at room temperature for 8 hours. The mixture was poured into ice water and washed with dichloromethane. The water layer was concentrated under reduced pressure and dried in vacuo. The residue was dissolved in N,N-dimethylformamide (150 ml), added dropwise with potassium carbonate (42 g, 304 mmol) and iodoethane (20.2 ml, 253 mmol). The mixture was then stirred for one day at 60° C. and poured into ice water. The solution was extracted with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (8.49 g, yield: 70%, yellow solid).

Provenance & Evidence