Hydrochloric Acid → 3-Bromo-6-chloro-2,4-dimethylpyridine

Temperature

0 °C

5-bromo-4,6-dimethylpyridin-2-amine (CAS No. 89856-44-0; Aldrich) (4.00 g) was added to a mixed solution of concentrated hydrochloric acid (24 mL) and water (24 mL). The solution was cooled to 0° C., and sodium nitrite (3.57 g) was added, followed by stirring at the same temperature for 10 minutes. Copper(I) chloride (5.91 g) was added to the solution, and the mixture was stirred at 0° C. for five minutes and at room temperature for four hours and 15 minutes. The reaction mixture was cooled to 0° C., and a 5 N aqueous sodium hydroxide solution was added to make the reaction mixture basic. Ethyl acetate was added to the reaction mixture, followed by filtration. The organic layer in the filtrate was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5%) to give the title compound (1.79 g).

1. stirringthe mixture was stirred at 0° C. for five minutes and at room temperature for four hours and 15 minutes
2. temperatureThe reaction mixture was cooled to 0° C.
3. filtrationfollowed by filtration
4. customThe organic layer in the filtrate was separated
5. extractionthe aqueous layer was extracted with ethyl acetate
6. concentrationThe combined organic layers were concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5%)

ORD record

ord-3869eada844f4c92b7c2e6eb275c24df

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563565B2