反应详情

温度

0 °C

Combine 4-fluoro-1-methyl-3-phenoxybenzene (2.43 g, 12.0 mmol), N-bromosuccinimide (4.92 g, 27.6 mmol), benzoyl peroxide (408 mg, 1.68 mmol), and carbon tetrachloride (55 mL). Heat the mixture at reflux temperature for 6.5 h and cool to 0° C. for 64 h. Filter the solids and concentrate the filtrate. Dissolve the residue in chloroform and wash with ice cold sodium carbonate solution. Dry the chloroform solution over sodium sulfate, filter and concentrate under reduced pressure. Dissolve the residue in acetonitrile (50 mL) and add 4-methylmorpholine-4-oxide (4.6 g, 39.1 mmol) and powdered 4 Å sieves (200 mg). Stir at ambient temperature for 20 h, filter and concentrate. Purify by silica gel chromatography (5%, 30% ethyl acetate/hexanes) to give 220 mg (8%) of the title compound: MS (m/e): 216 (M+).

1. temperatureHeat the mixture
2. temperatureat reflux temperature for 6.5 h
3. filtrationFilter the solids
4. concentrationconcentrate the filtrate
5. dissolutionDissolve the residue in chloroform
6. washwash with ice cold sodium carbonate solution
7. dry with materialDry the chloroform solution over sodium sulfate
8. filtrationfilter
9. concentrationconcentrate under reduced pressure
10. dissolutionDissolve the residue in acetonitrile (50 mL)
11. filtrationfilter
12. concentrationconcentrate
13. customPurify by silica gel chromatography (5%, 30% ethyl acetate/hexanes)