Chloroacetone → HCID 118006045, compound

A mixture of cloroacetone (17 mmol), LiBr (17 mmol) in acetonitrile (10 mL) was stirred at room temperature for 15 min. Then, a solution of 2-bromo-3-methylpyridine (19 mmol) in acetonitrile (10 mL) was added and the resulting mixture was heated at reflux for 24 h. The mixture was cooled to room temperature and the solvent was removed under reduce pressure. The residue was diluted with water extracted with diethylether. The aqueous was treated with K2CO3 (96 mmol) and heated at 80° C. for 2 h. The mixture was cooled to room temperature and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 35. (34%) 1H NMR (400 MHz, CDCl3) δ 7.76 (dt, J=6.9, 0.8 Hz, 1H), 7.20-7.07 (m, 1H), 6.83 (dd, J=7.1, 0.7 Hz, 1H), 6.40 (s, 1H), 6.25 (t, J=7.0 Hz, 1H), 2.39 (s, 3H). LC-MS (ES) for C9H8BrN [M+1]+ 209.11.

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 24 h
3. temperatureThe mixture was cooled to room temperature
4. customthe solvent was removed
5. additionThe residue was diluted with water
6. extractionextracted with diethylether
7. temperatureheated at 80° C. for 2 h
8. temperatureThe mixture was cooled to room temperature
9. extractionextracted with ethyl acetate (3×50 mL)
10. washThe combined organic layer was washed with brine
11. dry with materialdried over anhydrous Na2SO4
12. concentrationconcentrated by rotary evaporation
13. custompurified by column chromatography

ORD record

ord-993be7ae881d4069be8f250072a85b2f

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382245B2