4-chloro-5-fluoro-2-iodoaniline

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

Procedure: To Intermediate 5A (47 g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76 g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice water, then solid was filtered-off and washed with petroleum ether to afford 49 g of Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+. washed with petroleum ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-chloro-3-fluoroaniline (25 g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6 g, 0.25 mmol). After cooling to 0° C., iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A. MS (ESI) m/z: 145.2 (M+H)+. The reaction was extracted with DCM (4×250 mL) the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) dried (Na2SO4) Purification by silica gel chromatography

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

Procedure: To Intermediate 5A (47 g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76 g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice H2O, the solids were filtered-off and washed with petroleum ether to afford 49 g Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+. washed with petroleum ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-chloro-3-fluoroaniline (25 g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6 g, 0.25 mmol). After cooling to 0° C., iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A. MS (ESI) m/z: 145.2 (M+H)+. The reaction was extracted with DCM (4×250 mL) the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) dried (Na2SO4) Purification by silica gel chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-chloro-3-fluoroaniline (25 g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6 g, 0.25 mmol). After cooling to 0° C., iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A. MS (ESI) m/z: 145.2 (M+H)+. The reaction was extracted with DCM (4×250 mL) the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) dried (Na2SO4) Purification by silica gel chromatography

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

Procedure: To Intermediate 5A (47 g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76 g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice water, then solid was filtered-off and washed with petroleum ether to afford 49 g of Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+. washed with petroleum ether

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

Procedure: To Intermediate 5A (47 g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76 g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice water, then solid was filtered-off and washed with petroleum ether to afford 49 g of Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+. washed with petroleum ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-chloro-3-fluoroaniline (25 g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6 g, 0.25 mmol). After cooling to 0° C., iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A.MS (ESI) m/z: 145.2 (M+H)+. The reaction was extracted with DCM (4×250 mL) the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) dried (Na2SO4) Purification by silica gel chromatography

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

Procedure: To Intermediate 5A (47 g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76 g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice H2O, the solids were filtered-off and washed with petroleum ether to afford 49 g Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+. washed with petroleum ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-chloro-3-fluoroaniline (25 g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6 g, 0.25 mmol). After cooling to 0° C., iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A. MS (ESI) m/z: 145.2 (M+H)+. The reaction was extracted with DCM (4×250 mL) the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) dried (Na2SO4) Purification by silica gel chromatography

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

Procedure: To Intermediate 5A (47 g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76 g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice H2O, the solids were filtered-off and washed with petroleum ether to afford 49 g Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+. washed with petroleum ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-chloro-3-fluoroaniline (25 g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6 g, 0.25 mmol). After cooling to 0° C., iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A. MS (ESI) m/z: 145.2 (M+H)+. The reaction was extracted with DCM (4×250 mL) the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) dried (Na2SO4) Purification by silica gel chromatography