2,6-Dichloropyridine → HCID 57700380, compound

Temperature

0 °C

To a solution of 2,6-dichlorophenylacetic acid (4.1 g) in THF (100 mL) was added n-butyl lithium (1.4 M, in hexanes, 30 mL) slowly at 0° C. The resulting mixture was stirred at 0° C. for ½ hr and then cooled to −78° C. To this solution was added 2,6-dichloropyridine (2.96 g) at −78° C. then warmed to room temperature and stirred for approximately 1-3 hours. The mixture was re-cooled to −78° C. and oxalyl chloride (1.9 mL) was added. The resulting mixture was warmed to room temperature and stirred for 1 hr. The solution was re-cooled to −78° C. and ethynylmagnesium bromide (0.5 N, 44 mL) was added. The mixture was slowly warmed to room temperature. The reaction was quenched with 0.1 N HCl, and extracted with ether. The organic layer was separated, washed with brine solution, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by silica gel (hexanes/methylene chloride=3/1) to give desired compound as a yellowish solid (0.59 g).

1. temperaturecooled to −78° C
2. temperaturethen warmed to room temperature
3. stirringstirred for approximately 1-3 hours
4. temperatureThe mixture was re-cooled to −78° C.
5. temperatureThe resulting mixture was warmed to room temperature
6. stirringstirred for 1 hr
7. temperatureThe solution was re-cooled to −78° C.
8. temperatureThe mixture was slowly warmed to room temperature
9. customThe reaction was quenched with 0.1 N HCl
10. extractionextracted with ether
11. customThe organic layer was separated
12. washwashed with brine solution
13. dry with materialdried over magnesium sulfate
14. filtrationfiltered
15. customevaporated
16. customThe residue was purified by silica gel (hexanes/methylene chloride=3/1)

ORD record

ord-dc1ad8c370ee426e918674edc89a9dbc

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879875B2