Anisole → 4-Bromo-4'-methoxybenzophenone

To a solution of 4-bromo-benzoyl chloride (3.3 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 obtain the crude product which was purified by recrystallization from cyclohexane to yield the title product (4.0 g, 91%) as a solid; 1H NMR (500 MHz, CDCl3); δ 3.90 (s, 3H), 6.97 (d, J=8.5, 2H), 7.63 (d, J=2.0, 4H), 7.79 (d, J=9.0, 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. customand dried over anhy
4. customThe solvent was removed in vacuo
5. customto obtain the crude product which
6. customwas purified by recrystallization from cyclohexane

ORD record

ord-dcd0a86d7a764c75846d1b64edff917b

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402684B2