反应详情

Into a magnetically stirred suspension of 2,5-dimethyl-4-nitrophenol (12.70 grams, 75.98 mmol) in CH2Cl2 (150 milliliters) at room temperature was added portionwise N-bromosuccinimide (14.88 grams, 83.58 mmol). The mixture rapidly became homogeneous and after one hour thin layer chromatography (3:1 hexane:ethyl acetate) indicated complete consumption of the starting material and formation of a single major product. Saturated Na2SO3 solution (15 milliliters) was added and the solvent was removed under reduced pressure. Ethyl acetate was then added and the organic layer was washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure to afford 2-bromo-3,6-dimethyl-4-nitrophenol (13.6 grams, 55.3 mmol, 73%) as a rust colored solid. H'-NMR (CDCl3) 9.26 (brS, 1H), 7.71 (S, 1H), 2.60 (S, 3H), 2.31 (S, 3H).

1. customconsumption of the starting material and formation of a single major product
2. additionSaturated Na2SO3 solution (15 milliliters) was added
3. customthe solvent was removed under reduced pressure
4. additionEthyl acetate was then added
5. washthe organic layer was washed with water and brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure