methyl 5-chloro-2-iodobenzoate

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-chloro-2-iodobenzoic acid (3.0 g, 10.62 mmol), SOCl2 (12 mL) and DMF (0.6 mL) was gently warmed with a heat gun until the mixture became homogeneous (15 min). The solution was maintained at 23° C. for additional 30 min and then the solution was concentrated. MeOH (24 mL) was added to the crude residue and the solution was maintained at 23° C. for 30 min. The solution was concentrated and the residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15) to afford methyl 5-chloro-2-iodobenzoate (3.02 g, 10.20 mmol, 96%). (15 min) the solution was concentrated MeOH (24 mL) was added to the crude residue the solution was maintained at 23° C. for 30 min The solution was concentrated the residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15)

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-chloro-2-iodobenzoic acid (3.0 g, 10.62 mmol), SOCl2 (12 mL) and DMF (0.6 mL) was gently warmed with a heat gun until the mixture became homogeneous (15 min). The solution was maintained at 23° C. for additional 30 min and then the solution was concentrated. MeOH (24 mL) was added to the crude residue and the solution was maintained at 23° C. for 30 min. The solution was concentrated and the residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15) to afford methyl 5-chloro-2-iodobenzoate (3.02 g, 10.20 mmol, 96%). (15 min) the solution was concentrated MeOH (24 mL) was added to the crude residue the solution was maintained at 23° C. for 30 min The solution was concentrated the residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15)

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

Procedure: To a round bottomed flask was added NaHCO3 (22.31 g, 266 mmol), 5-chloro-2-iodobenzoic acid (25 g, 89 mmol), DMF, and MeI (11.07 mL, 177 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water (3×) and brine before being dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage to afford the titled compound (25.81 g, 87 mmol). LC/MS m/z 297 [M+H]+. The layers were separated the aqueous layer was extracted with EtOAc The combined organic layers were washed with water (3×) and brine before being dried over Na2SO4 filtered concentrated The crude residue was purified via Biotage

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

Procedure: To a round bottomed flask was added NaHCO3 (22.31 g, 266 mmol), 5-chloro-2-iodobenzoic acid (25 g, 89 mmol), DMF, and MeI (11.07 mL, 177 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water (3×) and brine before being dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage to afford the titled compound (25.81 g, 87 mmol). LC/MS m/z 297 [M+H]+. The layers were separated the aqueous layer was extracted with EtOAc The combined organic layers were washed with water (3×) and brine before being dried over Na2SO4 filtered concentrated The crude residue was purified via Biotage

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-chloro-2-iodobenzoic acid (3.0 g, 10.62 mmol), SOCl2 (12 mL) and DMF (0.6 mL) was gently warmed with a heat gun until the mixture became homogeneous (15 min). The solution was maintained at 23° C. for additional 30 min and then the solution was concentrated. MeOH (24 mL) was added to the crude residue and the solution was maintained at 23° C. for 30 min. The solution was concentrated and the residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15) to afford methyl 5-chloro-2-iodobenzoate (3.02 g, 10.20 mmol, 96%). (15 min) the solution was concentrated MeOH (24 mL) was added to the crude residue the solution was maintained at 23° C. for 30 min The solution was concentrated the residue was purified by flash chromatography on Biotage silica gel cartridge (cyclohexane to cyclohexane:EtOAc=85:15)