Sodium Sulfite → 5-Bromo-2-(((fluoromethyl)sulfonyl)methyl)pyridine

Temperature

100 °C

Commercially available fluoromethanesulfonyl chloride (975 mg, 7.36 mmol) is added dropwise to a solution of sodium sulfite (1.85 g, 14.7 mmol) and sodium bicarbonate (1.24 g, 14.7 mmol) in water (2 mL). The reaction mixture is heated in a microwave reactor to 100° C. for 20 minutes. After cooling to room temperature commercially available 5-bromo-2-(chloromethyl)pyridine (894 mg, 3.68 mmol) in ethanol (2 mL) is added. The mixture is heated in a microwave reactor to 100° C. for 20 minutes. The reaction mixture is cooled to 0° C. and the solid filtered off and discarded. The filtrates are diluted with saturated sodium carbonate (10 mL), extracted with tertiarybutyl methyl ether (50 mL). The organic layer is separated, dried over sodium sulfate, filtered and the solvent removed under reduced pressure to give the title compound (150 mg): m/z 268.9 (M+H)+.

1. additionis added
2. temperatureThe mixture is heated in a microwave reactor to 100° C. for 20 minutes
3. temperatureThe reaction mixture is cooled to 0° C.
4. filtrationthe solid filtered off
5. additionThe filtrates are diluted with saturated sodium carbonate (10 mL)
6. extractionextracted with tertiarybutyl methyl ether (50 mL)
7. customThe organic layer is separated
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customthe solvent removed under reduced pressure

ORD record

ord-f82baee5382e4004a99c8ca3ae5ebdd4

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206126B2