Hydrogen Peroxide → 3-(5-Bromo-2-fluorophenyl)pyridine-1-oxide

A mixture of 3-(5-bromo-2-fluorophenyl)pyridine (2.52 g, 10.0 mmol) and peracetic acid (3.37 ml of a 36-40 wt % solution in acetic acid) in tetrahydrofuran (40 ml) was stirred at ambient temperature for 1 h and then heated at 50° C. for 2 h. Hydrogen peroxide (35 wt % solution in water, 1 ml) was added and the mixture heated at 50° C. for a further hour. The solvent was removed in vacuo and the residue diluted with water and layered with ethyl acetate. Solid sodium hydrogencarbonate was added to pH 8. The layers were separated and the organic layer washed with water, brine, dried over anhydrous magnesium sulfate, filtered and pre-adsorbed onto silica. Purification by flash column chromatography on silica gel eluting with dichloromethane (containing 1% ammonia) on a gradient of methanol (2-5%) gave 3-(5-bromo-2-fluorophenyl)pyridine-1-oxide as a white solid (2.00 g, 75%): δH (400 MHz, CDCl3) 7.09-7.14 (1H, m), 7.35-7.43 (2H, m), 7.52-7.57 (2H, m), 8.22-8.25 (1H, m), 8.42 (1H, t, J 1).

1. temperatureheated at 50° C. for 2 h
2. temperaturethe mixture heated at 50° C. for a further hour
3. customThe solvent was removed in vacuo
4. additionthe residue diluted with water
5. additionSolid sodium hydrogencarbonate was added to pH 8
6. customThe layers were separated
7. washthe organic layer washed with water, brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered and pre-adsorbed onto silica
10. customPurification by flash column chromatography on silica gel eluting with dichloromethane (containing 1% ammonia) on a gradient of methanol (2-5%)

ORDレコード

ord-d0d063c6c1d04c39834c831292ec4114

出典データセット

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06900215B2