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ChemicalBook CAS DataBase List 2,6-Difluoronitrobenzene
19064-24-5

2,6-Difluoronitrobenzene synthesis

7synthesis methods
2,6-Difluoroaniline

5509-65-9

2,6-Difluoronitrobenzene

19064-24-5

Step 1: A mixture of sodium perborate tetrahydrate (65 g, 422 mmol) in glacial acetic acid (250 mL) was stirred at 80 °C. 2,6-Difluoroaniline (11.0 g, 85 mmol) was dissolved in glacial acetic acid (50 mL) and slowly added to the above mixture. The reaction temperature was maintained between 80-90°C for 1 hour. The cooled reaction mixture was poured into water and extracted twice with ether. The organic layers were combined, washed with dilute sodium bicarbonate solution, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified by a Biotage fast chromatography system (FlasH90i, silica gel column, 10% THF/hexane as eluent) and the product was washed with hexane to give 2,6-difluoronitrobenzene (7.0 g, 52% yield). Mass spectrum (ESI) m/z 160 ([M + H]+).

-

Yield:19064-24-5 52%

Reaction Conditions:

with sodium perborate in acetic acid at 80 - 90; for 1 h;

Steps:

99.1
Step 1: A mixture of sodium perborate tetrahydrate (65 g, 422 mmol) in glacial acetic acid (250 mL) was stirred at 80° C. 2,6-Difluoroaniline (11.0 g, 85 mmol) in glacial acetic acid (50 mL) was added slowly to the mixture. The temperature was maintained between 80-90° C. for 1 hour. The cooled reaction mixture was poured into water and extracted twice with diethyl ether. The combined organic layers were washed with a dilute solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and evaporated. The residue was purified via Biotage chromatography (FlasH90i, silica, 10% THF/hexane) and the product washed with hexane to afford 2,6-difluoronitrobenzene (7.0 g) (52%). MS (ESI) m/z 160 ([M+H]+).

References:

Wyeth US2005/222148, 2005, A1 Location in patent:Page/Page column 58

FullText

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