Benzoyl Peroxide → 5-(Bromomethyl)-2-chloro-3-fluoropyridine

Benzoyl peroxide (100 mg, 41 mmol) was added to a refluxing mixture of 2-chloro-3-fluoro-5-methylpyridine (5.0 g, 34.35 mmol) and NBS (6.73 g, 37.79 mmol) in CCl4 (180 mL). After stirring the mixture for 15 minutes, an additional amount of benzoyl peroxide (400 mg, 1.65 mmol) was added in four portions over a period of 1 hour and the stirring was continued for 1 hour. The reaction mixture was cooled to room temperature, filtered and the solid was washed with dichloromethane. The combined filtrates was washed with water, dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate) to afford 5-(bromomethyl)-2-chloro-3-fluoropyridine: 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J=2.0 Hz, 1H), 7.55 (dd, J=2.0, 8.8 Hz, 1H), 4.45 (s, 2H).

1. waitthe stirring was continued for 1 hour
2. filtrationfiltered
3. washthe solid was washed with dichloromethane
4. washThe combined filtrates was washed with water
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated on a rotary evaporator
7. customThe crude product was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-4a40868c14ea45028c0850e27c0bed3c

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919519B2