Hydrogen Peroxide → 3-Bromoquinolin-2-ol

Hydrogen peroxide solution (5.9 ml) was added to a THF solution (16 ml) of methyltrioxorhenium (VII) (24 mg). The mixture was stirred for 10 minutes at room temperature. 3-Bromoquinoline (4.0 g) was added thereto, and the mixture was stirred at room temperature for four days. Ethyl acetate (20 ml) was added to the reaction mixture. 20% Sodium sulfite aqueous solution (30 ml) was added slowly to the mixture under ice cooling. The mixture was stirred at room temperature. The organic layer was condensed to a half volume under reduced pressure. Ethyl acetate (20 ml) and 15% potassium carbonate aqueous solution (19 ml) were added thereto, and the organic layer was extracted. 15% Potassium carbonate aqueous solution (19 ml) of p-toluenesulfonyl chloride (4 g) were added thereto. The mixture was stirred for 10 minutes at room temperature. The generated insoluble matter was separated, washed with ethyl acetate, water, and then with ether, and dried to give the title compound (3.2 g) as a white powder.

1. stirringthe mixture was stirred at room temperature for four days
2. stirringThe mixture was stirred at room temperature
3. customcondensed to a half volume under reduced pressure
4. extractionthe organic layer was extracted
5. addition15% Potassium carbonate aqueous solution (19 ml) of p-toluenesulfonyl chloride (4 g) were added
6. stirringThe mixture was stirred for 10 minutes at room temperature
7. customThe generated insoluble matter was separated
8. washwashed with ethyl acetate, water
9. dry with materialwith ether, and dried

ORD record

ord-4619ec1e0624416bb44eb940d1a9c089

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822453B2