5-amino-2-bromo-4-methylbenzoic acid

To a solution of acid 24 (81 g, 535.8 mmol) in DMF (500 mL) was added NBS portionwise at 0 °C. The mixture was stirred at 0 °C for 70 min. The mixture was poured into Hthe bromination at the 6-position of 3-amino-4-methylbenzoic acid 23 using NBS yields bromide 24 in 89percent yieldTo a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (412.2 g, 2.72 mole) in DMF (2.2 L) was added N-bromosuccinimide (495.1 g, 2.78 mole) in small portions at such a rate that the reaction mixture temperature was kept below 15° C. To a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (412.2 g, 2.72 mole) in DMF (2.2 L) was added N-bromosuccinimide (495.1 g, 2.78 mole) in small portions at such a rate that the reaction mixture temperature was kept below 15° C. 5-Amino-2-bromo-4-methylbenzoic acid[0116] 3-amino-4-methylbenzoic acid (24.72 g, 162 mmol) was dissolved in anhydrous DMF (140 mL). The solution was then cooled to 0 - 5ºC and N-bromosuccinimide (29.70 g, 163.5 mmol) was added portionwise at a rate that the reaction mixture was kept below 15 ºC. The mixture was reacted for 2 hours and then poured into ice/water (150 g) with stirring. The produced solid was filtered and washed with cool water (3 x 120 mL). The filter cake was dissolved with EtOAc (800 mL) and washed with water (3 × 200 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford 5-amino-2-bromo-4-methylbenzoic acid as a pink solid (31.59 g, 85percent yield).In a round-bottom flask equipped with magnetic stirring and inert atmosphere, 3- amino-4-methylbenzoic acid (24.72 g, 162 mmol) was dissolved in anhydrous DMF (140 mL). The solution was then cooled to 0 - 5^C and /V-bromosuccinimide (29.70 g, 163.5 mmol) was added portionwise at a rate that the reaction mixture was kept below 15 2C. The mixture was reacted for 2 hours and then poured into ice/water (150 g) with stirring. The produced solid was filtered and washed with cool water (3 x 120 mL). The filter cake was dissolved with EtOAc (800 mL) and washed with water (3 x 200 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness under vacuum to afford 5-amino-2-bromo-4-methylbenzoic acid as a pink solid (31.59 g, 85percent yield).Step 1:

Molecular Weight:230.06
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:228.97384
Monoisotopic Mass:228.97384
Topological Polar Surface Area:63.3
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes