Dimethylformamide → 2-Bromo-5-[chloro(2,3,6-trifluorophenyl)methyl]-4-methylpyridine

To a solution of (6-bromo-4-methylpyridin-3-yl)(2,3,6-trifluorophenyl)methanol (4.60 g, 13.9 mmol) in methylene chloride (70 ml), thionyl chloride (10.1 ml, 139 mmol) and N,N-dimethylformamide (0.60 ml) were added at 0° C., and the resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the resulting residue, and subsequently water and then saturated aqueous sodium hydrogencarbonate were added thereto at 0° C. After the organic layer was separated, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was concentrated under reduced pressure, to obtain the title compound (4.65 g, 13.3 mmol, 96%) as a pale brown solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
2. additionwas added to the resulting residue, and subsequently water
3. additionsaturated aqueous sodium hydrogencarbonate were added
4. customat 0° C
5. customAfter the organic layer was separated
6. washthe organic layer was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-c475b54f790c45b6b85453fa1da99f89

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114886B2