4-CHLORO-3-CYANOMETHYL-BENZOIC ACID METHYL ESTER

Step 2: Intermediate 2 [00777j A mixture of Intermediate 1(1.00 g, 3.80 mmol), TMSCN (0.56 g, 5.69 mmol) and K2C03 (786 mg, 5.69 mmol) in CH3CN (50 mL) was refluxed for 16 h. The mixture was cooled to room temerpature, filtered and the filtrate was concentrated. The resultant residue was purified by column chromatography on silica gel (eluted with 5-10percent EtOAc in hexane) to afford the title compound (590 mg, 75 percent) as white solid. ‘H NMR (400 MHz, CDC13): ö 8.18 (d, 1H), 7.99 (dd, 1H), 7.52 (d, 1H), 3.94 (s, 3H), 3.88 (s, 2H).Preparation 3Methyl 4-chloro-3 -cy anomethy lbenzoateTo the solution of methyl 3-bromomethyl-4-chlorobenzoate (25.52 g) in dioxane (170 ml), cooled to 10 Preparation 6Methyl 4-chloro-3 -(cyanomethyl)benzoateA 10-litre glass reactor was equipped with a condenser, thermometer, dropping funnel and a mechanical stirrer. Step 2: Intermediate 2 [00777j A mixture of Intermediate 1(1.00 g, 3.80 mmol), TMSCN (0.56 g, 5.69 mmol) and K2C03 (786 mg, 5.69 mmol) in CH3CN (50 mL) was refluxed for 16 h. The mixture was cooled to room temerpature, filtered and the filtrate was concentrated. The resultant residue was purified by column chromatography on silica gel (eluted with 5-10% EtOAc in hexane) to afford the title compound (590 mg, 75 %) as white solid. 'H NMR (400 MHz, CDC13): oe 8.18 (d, 1H), 7.99 (dd, 1H), 7.52 (d, 1H), 3.94 (s, 3H), 3.88 (s, 2H).(i) Production of methyl 4-chloro-3-(1-cyano-1-methylethyl)benzoate; To a solution of

Molecular Weight:209.63
XLogP3:2.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:209.0243562
Monoisotopic Mass:209.0243562
Topological Polar Surface Area:50.1
Heavy Atom Count:14
Complexity:258
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes