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ChemicalBook CAS DataBase List 5-bromo-3-methylindolin-2-one
90725-49-8

5-bromo-3-methylindolin-2-one synthesis

11synthesis methods
-

Yield:90725-49-8 90 %

Reaction Conditions:

with hydrogen bromide;dihydrogen peroxide in 1,2-dimethoxyethane;water at 50;Green chemistry;

Steps:

4.2. General Procedure-1 for halide catalyzed oxidation

General procedure: To a 10 mL round-bottom flask equipped with a magnetic stir bar, indole (0.5 mmol), HBr (10 mol%, 0.05 mmol, 48%wt solution in water), and 1,2-dimethoxyethane (2.0 mL), were added. Then 30% hydrogen peroxide (77 mL, 0.75 mmol, 30% wt solution in water) was added dropwise. The reaction mixture was stirred for 30 min at 50 °C under air atmosphere. The reaction mixture was diluted by adding ethyl acetate and was quenched with a saturated aqueous solution of NaCl. Two layers were separated, and the aqueous layer extracted with ethyl acetate three times. The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to give oxindole product.

References:

Wang, Jian;Chen, Yini;Du, Wanting;Chen, Ningyao;Fu, Kang;He, Qijun;Shao, Liming [Tetrahedron,2022,vol. 127,art. no. 133101]