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ChemicalBook CAS DataBase List 2-AMINO-5-BROMOBENZOPHENONE

2-AMINO-5-BROMOBENZOPHENONE synthesis

13synthesis methods
2-Amino-5-bromobenzophenone is a benzophenone (B204980) derivative that is widely used in the synthesis of pharmaceutical compounds. It was prepared from 2-aminobenzonitrile sodium arylsulfinate, Pd(OAc)2 , bpy, and p-NBSA by stirring in a 2:1 mixture of THF/H2O for 48 h at 80℃.
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Yield: 90%

Reaction Conditions:

with p-nitrobenzenesulfonic acid;palladium diacetate in tetrahydrofuran;water at 80; for 48 h;Inert atmosphere;Schlenk technique;

Steps:

General Procedure for the Synthesis of o-Aminobenzophenones
General procedure: Under a N2 atmosphere, a Schlenk tube was charged with 2-aminobenzonitrile 1 (0.3 mmol),sodium arylsulfinate 2 (0.6 mmol), Pd(OAc)2 (10 mol %), bpy (20 mol %), p-NBSA (10 equiv), THF (2 mL), and H2O (1 mL) at room temperature. The reaction mixture was stirred vigorously at 80 °C for 48 h. The mixture was poured into ethyl acetate, which was washed with saturated NaHCO3 (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3.

References:

Chen, Jiuxi;Li, Jianjun;Su, Weike [Molecules,2014,vol. 19,# 5,p. 6439 - 6449]

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