反応 #1904053

反応方程式

Ethyl acetate

ammonium chloride

5-bromo anthranilic acid

methyllithium

→

title compound

収率 59.0%

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

収率 59.0%

溶媒

THF

反応条件

後処理

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

実験手順

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%).

出典