2-BROMOMETHYL-4-CHLORO-BENZOIC ACID METHYL ESTER

Compound C (10.86 g, 58.8 mmol, 1.0 eq.) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (15.7 g, 88.2 mmol., 1.5 eq.) was added followed by benzoylperoxide (0.05 g). The mixture was refluxed overnight. The reaction mixture was then filtered, and the solids were washed with dichloromethane. The combined organic filtrate was concentrated and dried to give compound D (7.1 g, 45.8percent). The structure was confirmed by Compound C (10.86 g, 58.8 mmol, 1.0 eq.) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (15.7 g, 88.2 mmol., 1.5 eq.) was added followed by benzoylperoxide (0.05 g). The mixture was refluxed overnight. The reaction mixture was then filtered, and the solids were washed with dichloromethane. The combined organic filtrate was concentrated and dried to give compound D (7.1 g, 45.8percent). The structure was confirmed by Step B 2-Bromomethyl-4-chloro-benzoic acid methyl ester; The compound from Step A (1.0 g, 5.4 mmol), N-bromosuccinimide (1.1 g, 6.0 mmol), and benzoylperoxide (catalytic amount) are refluxed overnight in carbon tetrachloride (10 mL) under nitrogen. Upon cooling the solid is removed by filtration and the filtrate is concentrated under reduced pressure. Ether is added, and the mixture is washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The remaining solid is triturated with hexane and collected by filtration providing the title compound (0.65 g, 45 percent). GC/MS: M-'*'263/264 ; HNMR (400 MHz, CDCl3).

Molecular Weight:263.51
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:261.93962
Monoisotopic Mass:261.93962
Topological Polar Surface Area:26.3
Heavy Atom Count:13
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes