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Chemical Structure| 855996-64-4 Chemical Structure| 855996-64-4

Structure of 855996-64-4

Chemical Structure| 855996-64-4

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Product Details of [ 855996-64-4 ]

CAS No. :855996-64-4
Formula : C7H6FNO3
M.W : 171.13
SMILES Code : O=C(C1C(F)=CC=CC=1O)NO
MDL No. :N/A

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Application In Synthesis of [ 855996-64-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 855996-64-4 ]

[ 855996-64-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 855996-64-4 ]
  • [ 178747-83-6 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25 - 60℃; for 7 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 15 - 20℃; for 1.25 h;
4-Fluorobenzo[d]isoxazol-3-ol (4): To a 20L jacketed reactor were charged tetrahydrofuran (2.23 L) and 1 ,1 '-carbonyldiimidazole (0.910 Kg, 5.64 mol). The resulting mixture was stirred at 20°C. Then a solution of 2-fluoro-N,6- dihydroxybenzamide (3) (744 g, 4.34 mol) in tetrahydrofuran (4.45 L) was slowly charged to the reactor maintaining the temperature below 30°C and stirred at 25°C for 30 min during which some off gassing was observed. The reaction mixture was heated to 60°C over 30 min and stirred for 6 h. The reactor was cooled to 20°C followed by the addition of 1 N aqueous hydrogen chloride (7.48L) over 15 min to adjust the pH to 1. The jacket temperature was set to 35°C and the reaction mixture concentrated under vacuum to remove approximately 6.68L of THF. The reactor was cooled to 15°C and stirred for 1 h. The resulting white slurry was filtered, the cake was washed with water (3.71 L) and dried in a vacuum oven at 40°C for 12 h. The desired product, (4) (597 g, 3.90 mol), was isolated in 90percent yield. 1 H NMR (400 MHz, CD3OD) δ ppm 4.93 (b, 1 H), 6.95 (dd, J=10.1 , 8.6, 1 H), (d, J=8.6, 1 H), 7.52-7.57 (m, 1 H); LRMS 154.029 (m+1 ).
References: [1] Patent: WO2011/101774, 2011, A1, . Location in patent: Page/Page column 25; 27.
 

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