反应详情

2-Methoxyaniline (o-anisidine) (15 g, 0.122 mol) was brominated with 2,4,4,6-tetrabromo-2,5-cyclohexadienone (50 g, 0.122 mol) by dissolving the aniline in 250 ml of methylene chloride, chilling the solution to -10°, and slowly adding and brominating agent, keeping the temperature below -5°. The reaction was allowed to warm at room temperature, and then washed with 2N sodium hydroxide (2×75 ml), then washed with water (2×25 ml), dried over magnesium sulfate, and evaporated to dryness. The product was purified on a silica gel column, eluted with methylene chloride giving 23.68 g (96%) of the title compound, mp 56.5°-58° (petroleum ether). Anal. Calcd for C7H8BrNO: C, 41.61; H, 3.99; Br, 39.55; N, 6.93. Found: C, 41.59; H, 3.99; Br, 39.49; N, 6.92.

1. temperaturechilling the solution to -10°
2. additionslowly adding
3. customthe temperature below -5°
4. washwashed with 2N sodium hydroxide (2×75 ml)
5. washwashed with water (2×25 ml)
6. dry with materialdried over magnesium sulfate
7. customevaporated to dryness
8. customThe product was purified on a silica gel column
9. washeluted with methylene chloride giving 23.68 g (96%) of the title compound, mp 56.5°-58° (petroleum ether)