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). 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).

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-0d3f6dc2f3624e9c92daa3c63d0c0cc1

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402684B2