2-BROMO-4-FLUORO-6-METHYLBENZOIC ACID

2-Bromo-4-fluoro-6-methylbenzoic acid2-Bromo-4-fluoro-6-methylbenzamide (0.9 g, 3.9 mmol) was dissolved in 75 percent aqueous sulfuric acid (4 mL) at 80 2-Bromo-4-fluoro-6-methylbenzamide (VIII) (0.9 g, 3.9 mmol) was dissolved in 75percent aqueous sulfuric acid (4 mL) at80 00 Sodium nitrite (0.5 g, 7.2 mmol) was carefully added in small portions during 1 h. The reaction mixture waschilled to 20 00 and cold water (15 ml) was added to the reaction mixture. The product was extracted with ethyl acetate (6 x 2 mL). The organic phase was washed with water (4 x 2 mL), brine (2 x 2 mL), dried over Na2504, filtered and concentrated to give 0.879 g (97percent) of pure acid (VII).1H NMR (400.5 MHz, DMSO-d6) ppm 2.31 (s, 1H), 7.22 (dd, JH-F = 9.6 Hz, JH-H = 2.2 Hz, 1H), 7.47 (dd, JH-F 8.5Hz, JH-H = 2.4 Hz, 1H), 13.7 (br. s, 1H).130 NMR (75.0 MHz, DMSO-d6+ 0014) ppm 19.5, 116.0 (d, JCF = 22Hz), 116.8 (d, JCF = 24Hz), 118.3 (d, JCF = 10Hz), 134.0 (d, JCF = 3 Hz), 138.4 (d, JCF = 8 Hz), 163.0 (d, JCF = 250 Hz), 168.0.2-Bromo-4-fluoro-6-methylbenzoic acid2-Bromo-4-fluoro-6-methylbenzamide (0.9 g, 3.9 mmol) was dissolved in 75 % aqueous sulfuric acid (4 mL) at 80 0C. sodium nitrite (0.5 g, 7.2 mmol) was carefully added in small portions during 1 hour. At the end of addition a persistent color of nitrogen dioxide appeared. The reaction mixture was chilled to 20 0C and cold water (15 mL) was added to the reaction mixture. The product was extracted with ethyl acetate (6 x 2 mL). The organic phase was washed with water (4 x 2 mL), brine (2 x 2 mL), dried with sodium sulfate, filtered and concentrated to give 0.879 g(97 %) of pure acid.1H NMR (400 MHz, DMSO-de) delta ppm 13.7 (br. s, 1H, OH), 7.47 (dd, 3JH-F = 8.5 Hz, 4JH-H = 2.4 Hz, 1H, Ar), 7.22 (dd, 3JH-F = 9.6 Hz, 4JH-H = 2.2 Hz, 1H, Ar), 2.31 (s, 1H, CH3). 13C NMR (300 MHz, DMSO-d6 + CCI4) delta ppm 168, 163 (d, 1Jc-F = 250 Hz), 138.4 (d, 3Jc-F = 8 Hz), 134 (d, 4Jc-F = 3 Hz), 118.3 (d, 3Jc-F = 10 Hz), 116.8 (d, 2Jc-F = 24 Hz), 116 (d, 19.5.2-Bromo-4-fluoro-6-methylbenzamide (VIII) (0.9 g, 3.9 mmol) was dissolved in 75% aqueous sulfuric acid (4 mL) at80 00 Sodium nitrite (0.5 g, 7.2 mmol) was carefully added in small portions during 1 h. The reaction mixture waschilled to 20 00 and cold water (15 ml) was added to the reaction mixture. The product was extracted with ethyl acetate (6 x 2 mL). The organic phase was washed with water (4 x 2 mL), brine (2 x 2 mL), dried over Na2504, filtered and concentrated to give 0.879 g (97%) of pure acid (VII).1H NMR (400.5 MHz, DMSO-d6) ppm 2.31 (s, 1H), 7.22 (dd, JH-F = 9.6 Hz, JH-H = 2.2 Hz, 1H), 7.47 (dd, JH-F 8.5Hz, JH-H = 2.4 Hz, 1H), 13.7 (br. s, 1H).130 NMR (75.0 MHz, DMSO-d6+ 0014) ppm 19.5, 116.0 (d, JCF = 22Hz), 116.8 (d, JCF = 24Hz), 118.3 (d, JCF = 10Hz), 134.0 (d, JCF = 3 Hz), 138.4 (d, JCF = 8 Hz), 163.0 (d, JCF = 250 Hz), 168.0.

Molecular Weight:233.03
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:231.95352
Monoisotopic Mass:231.95352
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes