ChemicalBook CAS DataBase List 5-Fluoro-2-nitrobenzoic acid

5-Fluoro-2-nitrobenzoic acid synthesis

4synthesis methods

Product Name:5-Fluoro-2-nitrobenzoic acid
CAS Number:320-98-9
Molecular formula:C7H4FNO4
Molecular Weight:185.11

455-38-9

320-98-9

a) General procedure for the synthesis of 5-fluoro-2-nitrobenzoic acid: 3-fluorobenzoic acid (7.9 g, 56 mmol) was dissolved in concentrated sulfuric acid (50 mL), and the solution was cooled to 0 °C. Fuming nitric acid (4.7 g, 67 mmol) was added dropwise with stirring. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the mixture was carefully poured into water (750 mL) and extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 5-fluoro-2-nitrobenzoic acid as a light yellow solid (9.6 g, 52 mmol, 93% yield).1H NMR (300 MHz, d6-DMSO) data for 5-fluoro-2-nitrobenzoic acid: δ 7.66 (m, 1H), 7.74 (m, 1H), 8.17 (m, 1H) ppm.

455-38-9 Synthesis

455-38-9
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$11.92/25g

320-98-9
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$8.00/5g

Yield:320-98-9 97%

Reaction Conditions:

with sulfuric acid;nitric acid

Steps:

17.A A.
A. 5-Fluoro-2-Nitrobenzoic Acid Fuming nitric acid (6.0 mL) was added to concentrated sulfuric acid (60 mL) at 0° C. and stirred for several minutes. To this solution was added 3-fluorobenzoic acid (5.60 g, 40 mmol) over 30 minutes and the reaction was allowed to continue for another 6 hours in an ice bath. The reaction was poured onto cracked ice, and the precipitate was collected by filtration and dried to give 5-fluoro-2-nitrobenzoic acid (7.20 g, 97%) as a white solid.: m.p. 118°-120°; 1H NMR (400 MH_z, DMSO-d6) δ 7.62 (dt, 1H), 7.71 (dd, 1H), 8.14 (dd, 1H); 13C NMR (100 MH_z, DMSO-d6) δ 117.1, 117.4, 119.2, 119.5, 127.6, 127.7, 131.5, 131.6, 144.5, 162.9, 165.4, 165.6.

References:

The Rockefeller University;Alteon Inc. US5514676, 1996, A

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