4-Bromoanisole → HCID 18322216, compound

Participants

Reaction Conditions

Reaction Steps

104 mg (4.28 mmol) of magnesium turnings in 10 ml of absolute diethyl ether were admixed with 0.79 g (4.27 mmol) of 4-bromoanisole. The reaction was started by addition of a drop of bromine. After about 2 h, the magnesium had completely dissolved. The mixture was cooled to 0° C. and 0.3 g (1.07 mmol) of N-(2-(3-methoxyphenyl)ethyl)phthalimide was added. The reaction mixture was allowed to warm to room temperature and, after 2 h, admixed with 5 ml of saturated sodium bicarbonate solution. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried and evaporated to dryness using a rotary evaporator. The resulting oil was purified by chromatography. Elution was carried out using a dichloromethanelmethanol gradient (0 to 2% methanol). The product, obtained as a colorless oils was foamed by coevaporation with diethyl ether. Yield: 0.32 g. M.p.: 119° C.

Provenance & Evidence