Sodium Methoxide → 3-Bromo-2-methoxy-5-(trifluoromethyl)pyridine

A mixture of 7.6 g of 2-chloro-3-bromo-5-(trifluoromethyl)pyridine, 6.2 ml of 25 percent sodium methoxide in methanol (0.027 mol), and 20 ml of anhydrous methanol was prepared and allowed to react at ambient temperature with stirring for 16 hours. The mixture was then poured onto ice and the resulting mixture extracted with ether. The ether extract was extracted with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure and the residue was purified by distillation under reduced pressure to obtain 4.1 g (65 percent of theory) of the title compound as a colorless oil boiling at 86°-88° C. at 21 mm pressure and having a refractive index at 19° C. of 1.4816. The proton nmr spectrum was consistent with the assigned structure.

1. customwas prepared
2. customto react at ambient temperature
3. additionThe mixture was then poured onto ice
4. extractionthe resulting mixture extracted with ether
5. extractionThe ether extract
6. extractionwas extracted with water
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated by evaporation under reduced pressure
9. distillationthe residue was purified by distillation under reduced pressure

ORD record

ord-ff25f26022d84622bd8d03d9acd9f24d

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04931452