2,6-Dichloro-4-cyanobenzoic acid

Step b: Synthesis of 2, 6-dichloro-4-cyanobenzoic acidA suspension of methyl 2, 6-dichloro-4-cyanobenzoate (620 mg, 2.6 mmol) in pyridine (5 ml_) was treated with anhydrous lithium iodide (1000 mg, 8 mmol). The resulting reaction mixture was stirred at reflux for 1 hour and concentrated under vacuum to remove pyridine. The residue was acidified with hydrochloric acid (2N) under ice-cold condition to adjust the pH between 2 to 3. The precipitated solid was filtered, washed with water and dried to yield 2, 6-dichloro-4-cyanobenzoic acid (380 mg, 86percent) as a pale brown solid.A suspension of methyl 2, 6-dichloro-4-cyanobenzoate (620 mg, 2.6 mmol) in pyridine (5 mL) was treated with anhydrous lithium iodide (1000 mg, 8 mmol). The resulting reaction mixture was stirred at reflux for 1 hour and concentrated under vacuum to remove pyridine. The residue was acidified with hydrochloric acid (2N) under ice-cold condition to adjust the pH between 2 to 3. The precipitated solid was filtered, washed with water and dried to yield 2, 6-dichloro-4-cyanobenzoic acid (380 mg, 86percent) as a pale brown solid. To a solution of methyl 2, 6-dichloro-4-cyanobenzoate (160 g, 694 mmol) in pyridine (1.5 L) at room temperature was added LiI (186 g, 1.39 mol). The mixture was heated under reflux for 2 hours, cooled to room temperature and concentrated under reduced pressure. The residue was treated with 2 N HCl (1 L) and the resulting precipitate was collected by filtration. The solid was recrystallized from DMF and water to give 2, 6-dichloro-4-cyanobenzoic acid (110 g, yield: 73percent) as a white solid.

Molecular Weight:216.02
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:214.9540837
Monoisotopic Mass:214.9540837
Topological Polar Surface Area:61.1
Heavy Atom Count:13
Complexity:248
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes