1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI) Chemical Properties

Melting point:

201-205℃

Density 

1.440±0.06 g/cm3 (20℃ 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

pka

12.98±0.20(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

HS Code 

2934999090

1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI) Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-fluorophenyl[d]isoxazol-3-one from 2-fluoro-N,6-dihydroxybenzamide is as follows: 1. Add tetrahydrofuran (2.23L) and 1,1'-carbonyl diimidazole (0.910Kg, 5.64mol) to a 20L jacketed reactor and mix with stirring at 20°C. 2. A solution of 2-fluoro-N,6-dihydroxybenzamide (744 g, 4.34 mol) in tetrahydrofuran (4.45 L) was slowly added to the reactor, the temperature was controlled to be lower than 30 °C, and stirring was continued at 25 °C for 30 h. The reaction was carried out at 25 °C with continuous stirring. Gas release was observed during the reaction. 3. The reaction mixture was warmed up to 60°C within 30 minutes and stirring was continued for 6 hours. 4. Upon completion of the reaction, the reactor was cooled to 20 °C and the pH was adjusted to 1 by adding 1N aqueous HCl (7.48 L) within 15 min. 5. set the jacket temperature to 35°C and concentrated the reaction mixture under vacuum to remove about 6.68 L of tetrahydrofuran. 6. The reactor was cooled to 15 °C and stirred for 1 h. A white slurry was obtained by filtration. The filter cake was washed with water (3.71 L) and dried in a vacuum oven at 40°C for 12 hours. 7. The target product 4-fluorobenzo[d]isoxazol-3-ol (597 g, 3.90 mol) was finally isolated in 90% yield. Product characterization data: 1H NMR (400MHz, CD3OD) δ ppm 4.93 (b, 1H), 6.95 (dd, J = 10.1, 8.6, 1H), (d, J = 8.6, 1H), 7.52-7.57 (m, 1H); LRMS 154.029 (m + 1).

References

[1] Patent: WO2011/101774, 2011, A1. Location in patent: Page/Page column 25; 27

1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI)(178747-83-6)Related Product Information

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