2-bromo-6-chloro-4-fluoroaniline

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-6-chloro-4-fluoroaniline (6.0 g, 26.7 mmol), zinc cyanide (11.42 g, 97.6 mmol) and Pd(PPh3)4 (2.16 g, 1.92 mmol) in anhydrous DMF (84 mL) was heated at 80° C., under an atmosphere of argon for 24 hours. The reaction mixture was cooled and diluted with brine. This mixture was extracted with ethyl acetate (×3) and the combined organic layers were washed with water (×2), dried, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane) to afford the title compound as a pale yellow solid (3.29 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ 7.27 (dd, J=7.9, 2.9 Hz, 1H), 7.08 (dd, J=7.6, 2.9 Hz, 1H), 4.67 (br s, 2H). The reaction mixture was cooled This mixture was extracted with ethyl acetate (×3) the combined organic layers were washed with water (×2) dried filtered concentrated under reduced pressure The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-6-chloro-4-fluoroaniline (6.0 g, 26.7 mmol), zinc cyanide (11.42 g, 97.6 mmol) and Pd(PPh3)4 (2.16 g, 1.92 mmol) in anhydrous DMF (84 mL) was heated at 80° C., under an atmosphere of argon for 24 hours. The reaction mixture was cooled and diluted with brine. This mixture was extracted with ethyl acetate (×3) and the combined organic layers were washed with water (×2), dried, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane) to afford the title compound as a pale yellow solid (3.29 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ 7.27 (dd, J=7.9, 2.9 Hz, 1H), 7.08 (dd, J=7.6, 2.9 Hz, 1H), 4.67 (br s, 2H). The reaction mixture was cooled This mixture was extracted with ethyl acetate (×3) the combined organic layers were washed with water (×2) dried filtered concentrated under reduced pressure The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-6-chloro-4-fluoroaniline (6.0 g, 26.7 mmol), zinc cyanide (11.42 g, 97.6 mmol) and Pd(PPh3)4 (2.16 g, 1.92 mmol) in anhydrous DMF (84 mL) was heated at 80° C., under an atmosphere of argon for 24 hours. The reaction mixture was cooled and diluted with brine. This mixture was extracted with ethyl acetate (×3) and the combined organic layers were washed with water (×2), dried, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane) to afford the title compound as a pale yellow solid (3.29 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ 7.27 (dd, J=7.9, 2.9 Hz, 1H), 7.08 (dd, J=7.6, 2.9 Hz, 1H), 4.67 (br s, 2H). The reaction mixture was cooled This mixture was extracted with ethyl acetate (×3) the combined organic layers were washed with water (×2) dried filtered concentrated under reduced pressure The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in cyclohexane)