反应 #1904053

反应方程式

Ethyl acetate

ammonium chloride

5-bromo anthranilic acid

methyllithium

→

title compound

收率 59.0%

1-(2-Amino-5-bromo-phenyl)-ethanone

收率 59.0%

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONAfter addition
2. 2
   其他organic layer was separated
3. 3
   萃取The aqueous layer was extracted with ethyl acetate (3×200 mL)
4. 4
   干燥The combined organic layers were dried (Mg2SO4)
5. 5
   浓缩concentrated
6. 6
   其他The residue was purified by a flash chromatography on silica gel (hexane:ethyl acetate/9:1)

实验过程

To a solution of 5-bromo anthranilic acid (50 g, 0.231 mol) in anhydrous THF (500 mL) at 0° C. under nitrogen was added in a dropwise manner methyllithium (1.4 M in diethyl ether, 661 mL, 0.926 mol). After addition, the reaction mixture was slowly allowed to warm to room temperature, stirred overnight, and treated with aqueous saturated ammonium chloride solution (1000 mL). Ethyl acetate (400 mL) was added and organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×200 mL). The combined organic layers were dried (Mg2SO4) and concentrated. The residue was purified by a flash chromatography on silica gel (hexane:ethyl acetate/9:1) to afford the title compound as a brown solid (29.3 g, 59%). MS (ES) m/z 214/216 ([M+H]+, 100%).

来源