Anisole → (4-Iodophenyl)(4-methoxyphenyl)methanone

Participants

Reaction Steps

To a solution of 4-iodo-benzoyl chloride (5 g, 15 mmol) and AlCl3 (2.6 g, 20 mmol) in nitrobenzene (20 mL) was added a solution of methoxy-benzene (1.5 g, 14.5 mmol) in nitrobenzene (5 mL) slowly at 0° C. The resulting mixture was allowed to warm to rt and stir at rt for 16 h. The mixture was poured onto 150 mL ice-water solution and extracted with CH2Cl2 (5×100 mL). The combined organic layers were washed with water (2×100 mL) and brine (50 mL) and dried over anhy. Na2SO4. The solvent was removed in vacuo to provide the crude product, which was purified by recrystallization from cyclohexane to yield the title product (4.8 g, 88%); MS, APCI+ (Calcd: 338.15. Found m/z: 339.35, M+1). 1H NMR (400 MHz, CDCl3); δ 3.89 (s, 3H), 6.96 (d, J=8.8, 2H), 7.47 (d, J=8.4, 2H), 7.79 (d, J=9.2, 2H), 7.83 (d, J=8.4, 2H).

Provenance & Evidence