2-Fluoro-4-nitrobenzoic acid

white to light yellow crystal powder

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 MgSOPeriodic 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 (2.x.30 mL) and water (2.x.30 mL). The organic layer was dried over MgSOA solution of 2-fluoro-4-nitro toluene (50 grams, 322.0 mmol) dissolved in a mixture of acetic acid (625 mL) and concentrated sulfuric acid (157 mL), was treated with an aqueous solution of chromium trioxide (116 grams, 1 160.0 mmol, in 100 mL water at 100 0C) for 3 hours. The reaction mixture was poured into ice-cold water (2 Litres) and extracted with diethyl ether (2 x 1 Litres). Evaporation of the volatiles left a residue, which was dissolved in 10percent aqueous potassiumcarbonate solution (1 Litre) and extracted with diethyl ether (300 mL). The aqueous layer was acidified with diluted hydrogen chloride and the solid obtained was filtered and dried. Yield: 66percent, MS (m/z): 186 (M++1), 1H NMR (300 MHz, CDCl3): δ 8.24 (dd, J= 1.6 7.0 Hz, IH), 8.14-8.04 (m, 2H).To a solution of sodium dichromate (3.87 g, 13 mmol) in acetic acid (20 mL) was added 2-fluoro-4-nitrotoluene (1.55 g, 10 mmol) in portions, followed by dropwise addition of concentrated sulfuric acid (10 g). A strong exotherm was observed (100° C.) and the color changed from orange to green. The reaction was heated at 90° C. for 1 hour and cooled to 25° C. The reaction mixture was dissolved in water (30 ml) and white crystals formed upon cooling at 0° C. The white solid was collected by filtration washed with cold water and dried to give 2-fluoro4-nitrobenzoic acid (0.99 g, 53percent). 1H NMR (DMSO-d6) δ: 8.16 (dd, J=10.0, 2.0 Hz, 1H), 8.10-8.03 (m, 2H).EXAMPLE 146 EXAMPLE 146 2-Flouro-4-nitro toluene (20 g) and sodium bromide (26.6 g) were added to deionized water (600 mL). Concentrated sulfuric acid (14 mL) was added to the reactionmixture and it was heated to 80°C to 85°C. A solution of potassium bromate (21.6 g) in de-ionized water (400 mL) was added to the reaction mixture over 3 hours. The reaction mixture was stirred for 24 hours and cooled to 20°C to 25°C. Ethyl acetate (300 mL) was added to the reaction mixture and it was stirred for 15 minutes. The layers obtained were separated. A solution of sodium hydroxide (10 g) in de-ionized water (300 mL) wasadded to the organic layer and it was stirred for 30 minutes. The layers obtained were separated and the aqueous layer was further washed with ethyl acetate (300 mL) to remove any undesired organic impurities. The aqueous layer was further acidified with concentrated hydrochloric acid (26 mL). Ethyl acetate (300 mL) was added to the aqueous layer. The ethyl acetate layer obtained was concentrated to obtain the title compound.Yield: 15.4 g.

Molecular Weight:185.11
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:185.01243577
Monoisotopic Mass:185.01243577
Topological Polar Surface Area:83.1
Heavy Atom Count:13
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes