Potassium Carbonate → 2-Chloro-3-(3,5-dibromophenoxy)-4-(trifluoromethyl)pyridine

To a round bottom flask charged with 3,5-dibromophenol (1.16 g, 4.61 mmol) and potassium carbonate (1.27 g, 9.22 mmol) was added N-methylpyrrolidinone (10 mL). To this suspension under N2 was added 2-chloro-3-fluoro-4-(trifluoromethyl)pyridine (0.920 g, 4.61 mmol) and the reaction mixture was placed in an oil bath at 120° C. After 30 minutes, the reaction mixture was allowed to cool to room temperature. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (3×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 120 gram column, eluting with 0-75% CH2Cl2 in hexanes to afford the title compound. 1H NMR (CDCl3) δ 8.53 (d, J=5.0 Hz, 1H), 7.62 (d, J=5.0 Hz, 1H), 7.44-7.42 (m, 1H), 6.92-6.88 (m, 2H). LRMS (M+1)=431.5.

1. customthe reaction mixture was placed in an oil bath at 120° C
2. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
3. washThe combined organic extracts were washed with brine (3×50 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customthe solvent was evaporated under reduced pressure
7. customThe resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 120 gram column
8. washeluting with 0-75% CH2Cl2 in hexanes

ORD record

ord-1326d49fefdf44908b6cff5dd1903f08

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404856B2