Ethyl2-cyano-5-fluorobenzoate synthesis

Yield:1260751-65-2 93%

Reaction Conditions:

with triphenylphosphine;tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ in N,N-dimethyl-formamide at 130; for 4 h;Inert atmosphere;

Steps:

2

Zinc cyanide (26.5 g; 0.225 mol) and Pd2(dba)3 (1.9 g; 3.4 mmol) were added to a solution of ethyl 2-bromo-5-fluorobenzoate (27.9 g; 0.112 mol) in DMF (71 ml). Triphenyl phosphine (2.9 g; 11 mmol) was added and then the reaction mixture was stirred at 130°C under nitrogen atmosphere for 4 hours. The mixture was poured out into H₂O (300 ml) and then extracted with EtOAc (200 ml). The organic layer was separated, washed with H₂O (2 x 100 ml), brine (100 ml), dried (MgSO₄), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: hexanes/EtOAc (5/1, v/v)). The product fractions were collected and the solvent was evaporated. Yield: 20 g (93%; orange solid).

References:

EP2487176,2012,A1 Location in patent:Page/Page column 17