2-fluoro-1-iodo-3-methoxybenzene

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

Procedure: In a reaction vial were placed aniline (0.200 g. 2.182 mmol); 2-fluoro-1-iodo-3-methoxybenzene (0.500 g., 1.984 mmol), Pd2(dba)3 (0.091 g. 0.099 mmol), BINAP (0.185 g, 0.298 mmol), NaOtBu (0.286 g. 2.98 mmol), and toluene (3 mL). The reaction was stirred at 80° C. overnight and quenched with water. The organic layer was separated and concentrated. The residue was purified by flash column chromatography to provide the title compound as a brown oil (0.313 g). LCMS m/z=218.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.82 (s, 3H), 6.73 (ddd, J=10.93, 8.15, 1.64 Hz, 1H), 6.88-7.05 (m, 3H), 7.15 (d, J=7.33 Hz, 2H), 7.25-7.31 (m, 2H), 7.80 (s, 1H). quenched with water The organic layer was separated concentrated The residue was purified by flash column chromatography

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

Procedure: In a reaction vial were placed aniline (0.200 g. 2.182 mmol); 2-fluoro-1-iodo-3-methoxybenzene (0.500 g., 1.984 mmol), Pd2(dba)3 (0.091 g. 0.099 mmol), BINAP (0.185 g, 0.298 mmol), NaOtBu (0.286 g. 2.98 mmol), and toluene (3 mL). The reaction was stirred at 80° C. overnight and quenched with water. The organic layer was separated and concentrated. The residue was purified by flash column chromatography to provide the title compound as a brown oil (0.313 g). LCMS m/z=218.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.82 (s, 3H), 6.73 (ddd, J=10.93, 8.15, 1.64 Hz, 1H), 6.88-7.05 (m, 3H), 7.15 (d, J=7.33 Hz, 2H), 7.25-7.31 (m, 2H), 7.80 (s, 1H). quenched with water The organic layer was separated concentrated The residue was purified by flash column chromatography

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

Procedure: In a reaction vial were placed aniline (0.200 g. 2.182 mmol); 2-fluoro-1-iodo-3-methoxybenzene (0.500 g., 1.984 mmol), Pd2(dba)3 (0.091 g. 0.099 mmol), BINAP (0.185 g, 0.298 mmol), NaOtBu (0.286 g. 2.98 mmol), and toluene (3 mL). The reaction was stirred at 80° C. overnight and quenched with water. The organic layer was separated and concentrated. The residue was purified by flash column chromatography to provide the title compound as a brown oil (0.313 g). LCMS m/z=218.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.82 (s, 3H), 6.73 (ddd, J=10.93, 8.15, 1.64 Hz, 1H), 6.88-7.05 (m, 3H), 7.15 (d, J=7.33 Hz, 2H), 7.25-7.31 (m, 2H), 7.80 (s, 1H). quenched with water The organic layer was separated concentrated The residue was purified by flash column chromatography

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

Procedure: In a reaction vial were placed aniline (0.200 g. 2.182 mmol); 2-fluoro-1-iodo-3-methoxybenzene (0.500 g., 1.984 mmol), Pd2(dba)3 (0.091 g. 0.099 mmol), BINAP (0.185 g, 0.298 mmol), NaOtBu (0.286 g. 2.98 mmol), and toluene (3 mL). The reaction was stirred at 80° C. overnight and quenched with water. The organic layer was separated and concentrated. The residue was purified by flash column chromatography to provide the title compound as a brown oil (0.313 g). LCMS m/z=218.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.82 (s, 3H), 6.73 (ddd, J=10.93, 8.15, 1.64 Hz, 1H), 6.88-7.05 (m, 3H), 7.15 (d, J=7.33 Hz, 2H), 7.25-7.31 (m, 2H), 7.80 (s, 1H). quenched with water The organic layer was separated concentrated The residue was purified by flash column chromatography