Dimethylformamide → 3-Fluoro-5-methoxy-4-nitrobenzonitrile

Participants

Reaction Steps

Into a microwave vial was added 5-bromo-1-fluoro-3-methoxy-2-nitrobenzene (1.75 g, 7.00 mmol), Pd(PPh3)4 (1.132 g, 0.9798 mmol), and zinc cyanide (0.8222 g, 7.002 mmol). The vial was sealed, and then DMF (28 mL) was added. The vial was evacuated and purged with N2 gas (3 times). The reaction mixture was irradiated on the microwave for 3-5 minutes at 150° C. The reaction mixture was quenched with water (30 mL) and then extracted with EtOAc (60 mL). The organic layer was washed with water (30 mL), brine (2×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a yellow oil. The crude material was purified by silica gel chromatography on an ISCO combi-flash Rf system using Heptane/EtOAc (100:0→55:45) as eluent to yield the desired product as a light yellow solid 1.15 g (84% yield). 1H NMR (CDCl3, 400 MHz): δ=4.01 (s, 3 H), 7.14 (t, J=1.52 Hz, 1 H), 7.19 (dd, J=8.21, 1.39 Hz, 1 H).

Provenance & Evidence