2-bromo-5-cyanobenzoic acid

To a suspension of copper (II) bromide (1.6 g, 7.1 mmol) in acetonitrile (30 ml) was added dropwise tert-butylnitrite (1.15 ml, 8. 63 mmol) at 0 °C within 2 minutes. 2- Amino-5-cyano-benzoic acid (CAS: 99767-45-0; W09518097) (1.0 g, 6.17 mmol) was added portionwise within 10 minutes at 0 °C. The mixture was stirred at 0 °C for 2 hours and then at room temperature overnight. Half of the solvent was removed in vacuo. The residue was taken in HCl 1N (15 ml) and ethyl acetate (30 ml). The organic layer was extracted with NAOH 1N (3X10 ml). The aqueous layer was acidified with HC1 2N. The resulting solid was filtered, washed with water and dried (high vacum, 50 °C) to provide the title compound (0.92 g, 66percent) as a yellow solid.A solution of NaNO2 (0.29 g, 4.2 mmol) in water (1 .6 mL) was added dropwise to a solution of 5-amino-2-bromobenzoic acid (0.86 g, 4 mmol) in HCl 2N (6 mL) and water (6 mL) at 0°C during 15 minutes. The reaction mixture was stirred for 20 minutes and then added dropwise to a solution of CuCN (0.7 g, 8 mmol) and NaCN (0.4 g, 8 mmol) in water (5 mL) at 60°C; the mixture was heated at 60 °C for further 15 minutes. After cooling at room temperature HCl (2N) was added and the product was extracted twice with AcOEt; the combined organic layers were dried and evaporated to give the title compound as a brown solid. Yield (0.6 g, 67percent). ESI- m/z 475 [2M+Na]A solution of NaNOA magnetically stirred mixture in dichloromethane of

Molecular Weight:226.03
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:224.94254
Monoisotopic Mass:224.94254
Topological Polar Surface Area:61.1
Heavy Atom Count:12
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes