反应详情

Methyl iodide (110 g was added dropwise to a stirred solution of 4-chloro-3-methylphenol (100 g) and potassium carbonate (194 g) in acetone (500 ml). The mixture was stirred for 1.5 hours. Methyl iodide (142 g) was added and the mixture stirred for a further hour. Solvent was removed by evaporation and the residue partitioned between water and ethyl acetate. The organic layer yielded an oil which was heated under reflux for 2 hours with N-bromosuccinimide (119 g) and benzoyl peroxide (1 g) in carbon tetrachloride (250 ml). The mixture was cooled, filtered and the filtrate concentrated to give a residue which was distilled under high vacuum. The fractions collected between 88° and 94° C./0.4 mbar were recrystallised from petroleum ether (b.p. 60°-80° C.) to give 2-chloro-5-methoxy benzyl bromide, m.p. 51°-52° C.

1. stirringthe mixture stirred for a further hour
2. customSolvent was removed by evaporation
3. customthe residue partitioned between water and ethyl acetate
4. customThe organic layer yielded an oil which
5. temperaturewas heated
6. temperatureThe mixture was cooled
7. filtrationfiltered
8. concentrationthe filtrate concentrated
9. customto give a residue which
10. distillationwas distilled under high vacuum
11. customThe fractions collected between 88° and 94° C./0.4 mbar
12. customwere recrystallised from petroleum ether (b.p. 60°-80° C.)