5-aMino-2-broMo-4-Methylbenzoic acid Methyl ester

To a cooled solution (5° C.) of 5-amino-2-bromo-4-methylbenzoic acid (100.0 g, 0.434 mmol) in anhydrous methanol (1.6 L) was added dropwise thionyl chloride (112.4 g). To a cooled solution (5° C.) of 5-amino-2-bromo-4-methylbenzoic acid (100.0 g, 0.434 mmol) in anhydrous methanol (1.6 L) was added dropwise thionyl chloride (112.4 g). 5-Amino-2-bromo-4-methylbenzoic acid methyl ester[0118] 5-amino-2-bromo-4-methylbenzoic acid (39.90 g, 0.17mol) was suspended in methanol (500 mL). The suspension was cooled to 0 to 5 ºC and thionyl chloride (40 mL, 0.54 mol) was added dropwise. The mixture was heated to reflux for 6 hours. The resulting solution was concentrated in vacuo and the residue was diluted with ice/water (500 g). The solution was neutralized to pH 7.5 with saturated aqueous NaHCOIn a round-bottom flask equipped with magnetic stirring and a reflux condenser with a calcium chloride tube, 5-amino-2-bromo-4-methylbenzoic acid (39.90 g, 0.17mol) was suspended in methanol (500 mL). The suspension was cooled to 0 to 5 and thionyl chloride (40 mL, 0.54 mol) was added dropwise. The mixture was heated to reflux for 6 hours. The resulting solution was concentrated under vacuum and the residue was diluted with ice/water (500 g). The solution was neutralized to pH 7.5 with saturated aqueous NaHC0Subsequent esterification under acidic conditions yields ester 25 in 92percent yield.Step 2:

Molecular Weight:244.08
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:242.98949
Monoisotopic Mass:242.98949
Topological Polar Surface Area:52.3
Heavy Atom Count:13
Complexity:198
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes