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

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); 1HNMR (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).

1. extractionextracted with CH2Cl2 (5×100 mL)
2. washThe combined organic layers were washed with water (2×100 mL) and brine (50 mL)
3. customdried over anhy
4. customThe solvent was removed in vacuo
5. customto provide the crude product, which
6. customwas purified by recrystallization from cyclohexane

ORD record

ord-313e13ab00f94972b274128478bf2d96

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598359B2