ChemicalBook CAS DataBase List 2-Fluoro-4-nitrobenzoic acid

2-Fluoro-4-nitrobenzoic acid synthesis

3synthesis methods

Product Name:2-Fluoro-4-nitrobenzoic acid
CAS Number:403-24-7
Molecular formula:C7H4FNO4
Molecular Weight:185.11

A mixture of 2-fluoro4-nitrotoluene (31.1 g, 0.2 mol), tetrabutylammonium bromide (3.2 g,0.01 mol), 1.0 L of 1N NaOH, and KMnO4 (20.0 g) was stirred at room temperature. After 10 min, the resulting mixture was heated to 95 °Cwith stirring. Additional 30.0 g portions of KMnO 4 were added after 2 h and 3 h. After stirring at 95 °C for an additional 10 h, the reaction mixture was cooled to room temperature and filtered through Celite to remove MnO2. The filtrate was acidified to pH 2 by adding concentrated hydrochloric acid. An off-white precipitate formed that was collected by vacuum filtration. The crude solid was dissolved in 300 mL of 1N aqueous NaOH, acidified to pH 2 using concentrated hydrochloric acid, and the mixture extracted with CH 2 Cl 2 (3 × 200 mL). The combined CH2 Cl 2extracts were washed with 0.1 N aqueous HCl (2 × 100 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to afford 27.3 g (73.7%)of 2-fluoro-4-nitrobenzoic acid as a white crystalline solid, m.p. 174.5–176.0 °C (lit 7. m.p. 176–177 °C)[1].

1427-07-2
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403-24-7
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Yield:403-24-7 81%

Reaction Conditions:

with chromium(VI) oxide;periodic acid in acetonitrile; for 1 h;

Steps:

56

Periodic acid (1.69 g, 7.41 mmol) was dissolved in acetonitrile (25 mL) by vigorous stirring, and then chromium trioxide (0.16 g, 1.60 mmol) was dissolved into the solution. 2-Fluoro-4- nitrotoluene (0.33 g, 2.13 mmol) was added to the above solution with stirring. A white precipitate formed immediately with exothermic reaction. After 1 h of stirring, the supernatant liquid of the reaction mixture was decanted to a flask, and the solvent was removed by evaporation. The residues were extracted with methylene chloride (2x30 mL) and water (2x30 mL). The organic layer was dried over MgSO₄, and concentrated to give 2-Fluoro-4-nitrobenzoic acid (Formula 37) (0.32 mg, 81%) as a white solid. ¹HNMR δ 8.06 (ddd, 1 H, J=9.9, 2.2 and 0.3), 8.13 (ddd, 1 H, /=8.6, 2.2 and 0.9), 8.25 (ddd, 1 H,J=8.6, 7.0 and 0.3).

References:

WO2006/124118,2006,A1 Location in patent:Page/Page column 78

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403-24-7
367 suppliers
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References

1427-07-2
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64-19-7 Synthesis

64-19-7
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403-24-7
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References

2-Fluoro-4-nitrobenzoic acid Related Search:

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