反应详情

温度

50 °C

To an aqueous solution of sodium hypochlorite (100.3 g, 134.7 mmol, 1.22 equiv.) and potassium bromide (13.5 g, 112.3 mmol, 1.02 equiv.) in sodium hydroxide solution (32%, 34.5 g, 276.0 mmol, 2.50 equiv.) was added slowly (during 35 min) at 50° C. 3-chloro-2-fluoro-5-trifluoromethyl-benzaldehyde (25.0 g, 110.4 mmol). The reaction mixture was stirred at 50° C. for 60 min, cooled to ambient temperature and quenched upon addition of sodium sulfite (60.4 g, 474.5 mmol, 4.3 equiv.) in water (450 ml) to give a clear yellow solution. The solution was treated with HCl (25%, 100 ml, 788.7 mmol, 7.14 equiv.) adjusting the pH to <2. The formed precipitate was extracted with toluene (300 ml), the organic phase was washed with a solution of sodium chloride (5%, 100 ml), dried over sodium sulfate and the solvents were removed under vacuum to give the crude product as light yellow solid. The crude product was dissolved in hot cyclohexane (125 ml), and the solution was cooled to ambient temperature, whereupon white crystals precipitated. The crystals were filtered off, washed with cyclohexane (25 ml) and dried under vacuum until weight constancy to give the title compound as white crystals (23.0 g, 85.8% yield). MS (EI): m/z 241.1 ([M−H]−, 100%). 1H-NMR (DMSO, 400 MHz): δ 14.08 (br s, 1H), 8.37-8.35 (dd, 1H), 8.11-8.09 (dd, 1H).

1. temperaturecooled to ambient temperature
2. customto give a clear yellow solution
3. extractionThe formed precipitate was extracted with toluene (300 ml)
4. washthe organic phase was washed with a solution of sodium chloride (5%, 100 ml)
5. dry with materialdried over sodium sulfate
6. customthe solvents were removed under vacuum
7. customto give the crude product as light yellow solid
8. temperaturethe solution was cooled to ambient temperature, whereupon white crystals
9. customprecipitated
10. filtrationThe crystals were filtered off
11. washwashed with cyclohexane (25 ml)
12. customdried under vacuum until weight constancy