Nitric Acid → HCID 68759685, compound

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL pear flask was charged 4-methoxyphenethyl bromide (0.727 ml, 4.65 mmol) in trifluoroacetic acid (9.30 ml). The solution was cooled to 0° C. In a 50 mL Erlenmeyer flask was added nitric acid (0.231 ml, 4.65 mmol) and trifluoroacetic acid (2.0 mL). The nitric acid solution was added to the reaction dropwise via syringe. The reaction was stirred at room temperature for 2 hours. The solvent was removed on a rotovap and the residue taken up into ethyl acetate. The reaction was washed with 1N HCl, saturated aqueous sodium bicarbonate, and brine, dried over MgSO4, filtered and concentrated onto silica gel. The reaction was purified by flash chromatography (10% ethyl acetate:hexanes for 20 minutes, then to 50% ethyl acetate:hexanes over 20 minutes) to provide the title compound. MS (DCI) m/e 277 (M+NH4).

Provenance & Evidence