2-BROMO-4-NITROBENZOIC ACID

Light Brown Solid

To a mixture of 2-bromo-4-nitrotoluene (25g, 116mmol), pyridine (100mL) and water (200mL) was added KMnO(a) Compound 21 used in the preparation of compound 24 was prepared as follows. 2-bromo-4-nitrobenzoic Acid Intermediate 10A. 2-Bromo-4-nitro-benzoic acid: To a warm (80 °C) solution of pyridine (500 mL) and water (1 L) was added 4-nitro-2-bromo toluene (100 g, 0.46 mol). The resulting suspension was stirred until it became a clear solution. To the above reaction mixture was then added KMn04 (600 g, 3.8 mol) in portions over 1.5 h and stirring was continued overnight. The reaction mixture was then cooled to rt and then 10percent aqueous NaOH (200 mL) was added. After 15 min, the reaction was filtered to remove the solids. The solids were then rinsed with 10percent aqueous NaOH (5x100 mL). The filtrate was extracted with MTBE (3x250 mL). The clear aqueous layer was cooled to 10 °C and then it was acidified with concentrated HC1. The aqueous layer was again extracted with MTBE (4x500 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to afford 72 g of Intermediate 10A. 1H NMR (400 MHz, DMSO-d6) δ 7.96 (d, J = 8 Hz, 1H), 8.28 - 8.48 (m, 1H), 8.49 (d, J = 2.4 Hz, 1H), 14.1 (br. s, 1H) ppm.[00355] Intermediate 18 A. 2-Bromo-4-nitro-benzoic acid: To a warm (80 °C) solution of pyridine (500 mL) and water (1 L) was added 4-nitro-2-bromo toluene (100 g, 0.46 mol). The resulting suspension was stirred until it became a clear solution. To the above reaction mixture was then added KMn04 (600 g, 3.8 mol) in portions over 1.5 h and stirring was continued overnight. The reaction mixture was then cooled to rt and then 10percent aqueous NaOH (200 mL) was added. After 15 min, the reaction was filtered and the solid was rinsed with 10percent> aqueous NaOH (5x100 mL). The filtrate was extracted with MTBE (3x250 mL). The clear aqueous layer was cooled to 10 °C and then it was acidified with concentrated HC1. The aqueous layer was again extracted with MTBE (4x500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 72 g of Intermediate 18A. 1H NMR (400 MHz, DMSO-d6) δ 7.96 (d, J= 8 Hz, 1H), 8.28 - 8.48 (m, 1H), 8.49 (d, J= 2.4 Hz, 1H), 14.1 (br. s, lH) ppm.

Molecular Weight:246.01
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:244.93237
Monoisotopic Mass:244.93237
Topological Polar Surface Area:83.1
Heavy Atom Count:13
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes