4-Ethylbenzoic Acid → (5-Bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone

To a solution of 4-ethyl benzoic acid (AQ) (0.50 g, 3.33 mmol) in dry dichloromethane (20 mL) was added dropwise oxalyl chloride (0.32 mL, 3.68 mmol) followed by N,N-dimethylformamide (0.1 mL). After being stirred for 2 h at room temperature, the reaction mixture was evaporated and the residue was dissolved in dry dichloromethane (20 mL) at room temperature under agron. After cooling to −5° C., 1-bromo-4-chloro-2-methoxybenzene (0.6 g, 2.78 mmol) was added. Then AlCl3 (0.43 g, 3.33 mmol) was added portionwise and the reaction temperature was kept between −5° C. and 0° C. After being stirred at room temperature for four hours, the reaction mixture was poured onto ice water and extracted with dichloromethane (80 mL). The combined organic layers were washed with 1 M HCl (10 mL), water (10 mL) and brine (10 mL), and then dried over anhydrous Na2SO4 Concentration under reduced pressure gave AR as a white solid. Yield: 0.5 g (52.3%). 1H-NMR (CDCl3, 400 MHz): δ 7.75 (d, J=8.4 Hz, 2H), 7.60 (s, 1H), 7.32 (d, J=8.0 Hz, 2H), 6.98 (s, 1H), 3.99 (s, 3H), 2.76 (q, J=7.5 Hz, 2H), 1.29 (t, J=7.5 Hz, 3H).

1. customthe reaction mixture was evaporated
2. dissolutionthe residue was dissolved in dry dichloromethane (20 mL) at room temperature under agron
3. temperatureAfter cooling to −5° C.
4. customwas kept between −5° C. and 0° C
5. stirringAfter being stirred at room temperature for four hours
6. additionthe reaction mixture was poured onto ice water
7. extractionextracted with dichloromethane (80 mL)
8. washThe combined organic layers were washed with 1 M HCl (10 mL), water (10 mL) and brine (10 mL)
9. dry with materialdried over anhydrous Na2SO4 Concentration under reduced pressure
10. customgave AR as a white solid

ORD record

ord-d5fff5fc1791424b8395a5f025ac52c8

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07838498B2