5-Fluoro-2-methyl-3-nitrobenzoic acid

116 ml of sulfuric acid is introduced and mixed in portions at -15° C. with 14.70 g (95.37 mmol) of 5-fluoro-2-methylbenzoic acid. A mixture of nitrating acid (4.79 ml of fuming nitric acid and 21.8 ml of concentrated sulfuric acid) is added in drops to this mixture, specifically at -15 to -110° C. for a period of 90 minutes. After three more hours of stirring, the reaction mixture is poured into ice water and stirred vigorously for about one-half hour. The precipitated crystallizate is suctioned off, washed neutral with water and dried. The yield is 8.56 g (45.1percent) of a mixture of various regioisomers and by-products. This mixture is thus used in the next stage (esterification) and purified in this stage.5-Fluoro-2-methylbenzoic acid (20 g) was added portionwise to ice-cooled conc. sulfuric acid (98 80 mL) . The mixture was stirred at 0 until all solid dissolved. A mixture of nitric acid (65 6 mL) and H5-Fluoro-2-methylbenzoic acid (20 g) was added portionwise to ice-cooled conc. sulfuric acid(98percent, 80 mL). The mixture was stirred at 0°C until all solid dissolved. A mixture of nitric acid (65percent, 6 mL) and H2S04 (98percent, 12 mL) was added portionwise. The mixture was allowed to warm gradually to RT, and stirred at RT for 6 hours. The resulting mixture was poured into ice (500 mL). The solid was collected and washed with water (100 mL). The solid was redissolved in EA (200 mL) and washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentratedin vacuo to afford the title compound (11 g) as brown solid. MS (ESI): C8H6FNO4 requires 199; found 198 [M-Hf.Description 1355-Fluoro-2-methyl-3-nitrobenzoic acid (D135)O2NIOH5-Fluoro-2-methylbenzoic acid (20 g) was added portion-wise to ice-cooled con. sulfuric acid (98percent, 80 mL), the mixture was stirred at 0°C until all solid dissolved, and then the mixture of nitric acid(65percent, 6 mL) and H2504 (98percent, 12 mL) was added portion-wise, the mixture was warmed gradually to RT and stirred at RT for 6 hours. The mixture was poured into ice (500 g), the resulting solid was collected and washed with water (100 mL), the solid was re-dissolved in EtOAc (200 mL) and washed with brine. The organic layer was dried over anhydrous Na2SO4. Filtered, the filtrate was concentrated under vacuum to afford the title compound (11 g) as brown solid. 1H NMR (400 MHz, MeOD-d4): 7.84 (dd, J= 8.7, 2.6 Hz, 1H), 7.78 (dd, J= 7.8, 2.8 Hz, 111), 2.55 (s, 3H). MS (ESI):C8H6FNO4 requires 199; found 198 [M-Hf.5-fluoro-2-methylbenzoic acid (20 g)To ice-cooled concentrated sulfuric acid (98percent, 80 mL).The mixture was stirred at 0 ° C until all solids were dissolved.A mixture of nitric acid (65percent, 6 mL) and H2SO4 (98percent, 12 mL) was added in portions, And then let it slowly rise to RT.The resulting mixture was stirred at room temperature for 6 hours, Then poured into ice (500 mL).The solid was collected and washed with water (100 mL). The solid was again dissolved in ΕΑ (200 mL) and washed with brine. The organic layer was dehydrated with anhydrous Na2S04 and concentrated in vacuo to give the title compound (11 g) as a brown solid

Molecular Weight:199.14
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:199.02808583
Monoisotopic Mass:199.02808583
Topological Polar Surface Area:83.1
Heavy Atom Count:14
Complexity:252
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes