Dimethylformamide → Methyl 2-chloro-5-cyanobenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-bromo-2-chlorobenzoate (2 g; 8.02 mmol; 1 eq.), zinc cyanide (564.79 mg; 4.81 mmol; 0.60 eq.), tris(dibenzylideneacetone)dipalladium(0) (58.73 mg; 0.06 mmol; 0.01 eq.), 1,1′-bis(diphenylphosphino)ferrocene (71.11 mg; 0.13 mmol; 0.02 eq.), zinc (20.97 mg; 0.32 mmol; 0.04 eq.) and zinc acetate (58.83 mg; 0.32 mmol; 0.04 eq.) were put in dry DMF (20 mL). The reaction mixture was purged with N2 and then heated to 90° C. for 3 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with EtOAc. The organic phase was washed with water, brine, dried over MgSO4 and concentrated to afford a brown solid purified by flash chromatography eluting with cHex-EtOAc 8:2 affording the title compound as a yellow solid. It was washed with EtOH and dried under vacuum affording the title compound as a yellow solid (1.55 g, 98%). 1H NMR (DMSO-d6, 300 MHz) δ 8.29 (m, 1H), 8.09-8.06 (m, 1H), 7.83-7.81 (m, 1H), 3.89 (s, 3H). LC/MS (Method B): 197.0 (M+H)+. HPLC (Method A) Rt 3.70 min (Purity: 83.7%)

Provenance & Evidence