2-Fluoro-5-nitrobenzoic acid synthesis
- Product Name:2-Fluoro-5-nitrobenzoic acid
- CAS Number:7304-32-7
- Molecular formula:C7H4FNO4
- Molecular Weight:185.11
445-29-4
7304-32-7
General procedure for the synthesis of 2-fluoro-5-nitrobenzoic acid from o-fluorobenzoic acid: Nitric acid (60% solution, 5.0 mL) was slowly added dropwise to pre-cooled concentrated sulfuric acid (5.0 mL), and the reaction temperature was controlled to not exceed 10 °C. Subsequently, o-fluorobenzoic acid (2.1 g, 15.0 mmol) was added in batches and the reaction temperature was maintained between 15 and 25 °C. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction was quenched by addition of ice water and the precipitate was collected by filtration. The product was dried at room temperature to give the intermediate 2-fluoro-5-nitrobenzoic acid as a white powder. Yield: 93%; Melting point: 135-137 °C; 1H NMR (300 MHz, DMSO-d6): δ=7.32 (t, 1H, H3, 3JH3_H4=JH3-F=9.2 Hz), 8.43 (dt, 1H, H4, 3JH4_H3=9.2 Hz, 4JH4_F=4JH4_H6=3.5 Hz), 8.89 (dd, 1H, H6, 4JH6_F=5.8 Hz, 4JH6_H4=3.0 Hz); 13C NMR (75 MHz, DMSO-d6): δ=118.7 (d, C1, 2JC-F=10.9 Hz), 118.7 (d, C3, 2JC-F=25.0 Hz), 128.9 (d, C6, 3JC -F=2.2 Hz), 130.6 (d, C4, 3JC-F=10.9 Hz), 143.9 (C5), 165.7 (d, C2, 1JC-F=272.0 Hz), 166.7 (d, COOH, 3JC-F=3.8 Hz).
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Yield:7304-32-7 93%
Reaction Conditions:
with sulfuric acid;nitric acid at 10 - 25; for 2 h;
Steps:
A35.A35-a
A35-a intermediate 36: 2-Fluoro- -nitrobenzoic acidNitric acid (60% solution, 5.0 mL) was carefully added to a cooled solution of concentrate sulfuric acid (5.0 mL) so that the temperature did not exceed 10 °C. 2-f uorobenzoic acid (2.1 g, 15.0 mmol) was added by small portions while maintaining temperature between 15 and 25 °C. The mixture was stirred for 2 h at room temperature. Ice was added and the precipitate was filtered. After drying at room temperature, intermediate 36 was obtained as a white powder. Yield: 93%; mp 135-137 °C; 1H NMR (300 MHz, OMSO-d6): δ = 7.32 (t, 1 H, H3, 3 J H3_H4 = J H3-F = 9.2 Hz), 8.43 (dt, 1 H, H JH4.H3 = 9.2 Hz, JH4.F = JH4.H6 = 3.5 Hz), 8.89 (dd, 1H, ¾, 4JH6.F = 5.8 Hz, 4JH6.H4 = 3.0 Hz); 13C NMR (75 MHz, DMSO- d6): δ = 118.7 (d, Ci, 2JC-F = 10.9 Hz), 118.7 (d, C3, 2JC-F = 25.0 Hz), 128.9 (d, C6> 3JC-F = 2.2 Hz), 130.6 (d, C4, 3JC- = 10.9 Hz), 143.9 (C5), 165.7 (d, C2, 1JC.F = 272.0 Hz), 166.7 (d, COOH, 3Jc- = 3.8 Hz).
References:
KATHOLIEKE UNIVERSITEIT LEUVEN, K.U. LEUVEN R&D;UNIVERSITE DE LILLE;CENTRE NATIONAL DE RECHERCHE SCIENTIFIQUE;ECOLE NATIONALE SUPERIEURE DE CHIMIE DE LILLE;BAILLY, Fabrice;BILLAMBOZ, Muriel;CHRIST, Frauke;COTELLE, Philippe;DEBYSER, Zeger;LION, Cédric;SUCHAUD, Virginie WO2012/85003, 2012, A1 Location in patent:Page/Page column 83
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7304-32-7
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445-29-4
430 suppliers
$5.00/10g
7304-32-7
269 suppliers
$8.00/10g