Hydrochloric Acid → HCID 13408303, compound

Participants

Reaction Conditions

Reaction Steps

To a boiling mixture of p-anisidine (2.46 g, 20 mmol, 6.66 eq) and N,N-dimethylaniline (3.5 ml) is slowly added dropwise 2-bromo-4-methoxyacetophenone (0.7 g, 3 mmol, 1 eq) dissolved in ethyl acetate (12 ml). After the addition is complete, the reaction mixture is stirred at 180° C. for 2 h. To the cooled mixture are added ethyl acetate and 2 M HCl. The aqueous phase is extracted with ethyl acetate several times, and the combined organic phases are washed with a saturated NaCl solution, dried over MgSO4, filtered and evaporated to dryness on a rotary evaporator. Purification by column chromatography (eluent dichloromethane/hexane 7/3) yields the desired product in a yield of 15% (760 mg).

Provenance & Evidence