Methyl 2-chloro-4-fluorobenzoate

A mixture of 2-chloro-4-fluorobenzoic acid (6.5 g, 37 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (14.0 mL, 111 mmol), stirred 24h at room temperature and evaporated. The residue was dissolved in dichloromethane, washed with sodium bicarbonate, dried (sodium sulfate) and evaporated to provide 2-chloro-4-fluoro-benzoic acid methyl ester (7.01 g, 99percent yield) as a pale yellow oil. 1H-NMR (CDCl3, 500 MHz) 7.93 (m, 1H), 7.22 (m, 1H), 7.06 (m, 1H), 3.95 (s, 3H) ppm; MS (FIA) 189.1 (M+H); HPLC (Method A) 3.37 min.General procedure: To a mixture of the appropriate substituted benzoic acid (8.6 mmol) in methanol (10 mL) was added sulfuric acid (0.5 mL), and the mixture was heated overnight at 60 °C. The reaction was then allowed to cool to room temperature, the solvent was reduced by evaporation, and the residue was diluted in cold water and neutralized with sodium hydrogen carbonate solution. The aqueous solution was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous MgSO

Molecular Weight:188.58
XLogP3:3.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:188.0040353
Monoisotopic Mass:188.0040353
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes