Dimethylformamide → Methyl 2-chloro-4-cyano-5-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-bromo-2-chloro-5-fluorobenzoate (1.80 g; 6.73 mmol; 1 eq.), zinc cyanide (474.13 mg; 4.04 mmol; 0.60 eq.), tris(dibenzylideneacetone)dipalladium(0) (49.30 mg; 0.05 mmol; 0.01 eq.), 1,1′-bis(diphenylphosphino)ferrocene (59.69 mg; 0.11 mmol; 0.02 eq.), zinc (17.60 mg; 0.27 mmol; 0.04 eq.) and zinc acetate (49.39 mg; 0.27 mmol; 0.04 eq.) were put in dry DMF (18 mL). The reaction mixture was purged with N2 and then heated to 90° C. for 12 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 affording a brown solid. It was purified by washing with EtOH affording the title compound as a beige solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.37-8.35 (d, J=5.86 Hz, 1H), 8-7.97 (d, J=9.18 Hz, 1H), 3.91 (s, 3H).

Provenance & Evidence