2,4-dichloro-3-iodoaniline

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

Procedure: To a solution of 2,4-dichloro-3-iodoaniline (9.0 g, 31 mmol) in DME/water (180 mL/60 mL) is added vinyl triboroxine pyridine complex (5.0 g, 20.8 mmol) and K2CO3 (8.5 g, 62.0 mmol). The reaction mixture is stirred and N2 is bubbled in for 15 min. Tetrakis(triphenylphosphine) palladium(0) (1.8 g, 1.6 mmol) is added at room temperature and N2 is bubbled in for additional 20 min. The reaction mixture is heated to 80° C. and stirred for 18 hours, when the GC-MS showed the reaction is complete. The mixture is filtered and washed with ether (400 mL) and water (50 mL). The organic layer is separated and washed with brine and dried over MgSO4. The solvents were removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-vinylaniline. N2 is bubbled in for 15 min N2 is bubbled in for additional 20 min stirred for 18 hours The mixture is filtered washed with ether (400 mL) and water (50 mL) The organic layer is separated washed with brine dried over MgSO4 The solvents were removed the residue is purified through a flash chromatographic column with a gradient of hexanes/ether

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

Procedure: To a solution of N-(2,4-dichloro-3-iodophenyl)acetamide (40.0 g, 121 mmol) in MeOH (100 mL) is added concentrated HCl (50 mL). The mixture is stirred and heated at reflux for 18 hours. The mixture is cooled and the solvents were removed under reduced pressure (water bath below 45° C.). The residue is cooled with an ice bath and 3N NaOH solution was added to adjust the pH to between 9 and 10. The mixture is extracted with ether and dried over MgSO4. The solvents were removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-iodoaniline. heated at reflux for 18 hours The mixture is cooled the solvents were removed under reduced pressure (water bath below 45° C.) The residue is cooled with an ice bath 3N NaOH solution was added The mixture is extracted with ether dried over MgSO4 The solvents were removed the residue is purified through a flash chromatographic column with a gradient of hexanes/ether

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

Procedure: To a solution of 2,4-dichloro-3-iodoaniline (9.0 g, 31 mmol) in DME/water (180 mLU60 mL) is added vinyl triboroxine pyridine complex (5.0 g, 20.8 mmol) and K2CO3 (8.5 g, 62.0 mmol). The reaction mixture is stirred and N2 is bubbled in for 15 min. Tetrakis(triphenylphosphine) palladium(0) (1.8 g, 1.6 mmol) is added at room temperature and N2 is bubbled in for additional 20 min. The reaction mixture is heated to 80° C. and stirred for 18 hours, when the GC-MS showed the reaction is complete. The mixture is filtered and washed with ether (400 mL) and water (50 mL). The organic layer is separated and washed with brine and dried over MgSO4. The solvents were removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-vinylaniline. N2 is bubbled in for 15 min N2 is bubbled in for additional 20 min stirred for 18 hours The mixture is filtered washed with ether (400 mL) and water (50 mL) The organic layer is separated washed with brine dried over MgSO4 The solvents were removed the residue is purified through a flash chromatographic column with a gradient of hexanes/ether

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

Procedure: To a solution of N-(2,4-dichloro-3-iodophenyl)acetamide (40.0 g, 121 mmol) in MeOH (100 mL) is added concentrated HCl (50 mL). The mixture is stirred and heated at reflux for 18 hours. The mixture is cooled and the solvents were removed under reduced pressure (water bath below 45° C.). The residue is cooled with an ice bath and 3N NaOH solution was added to adjust the pH to between 9 and 10. The mixture is extracted with ether and dried over MgSO4. The solvents were removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-iodoaniline. heated at reflux for 18 hours The mixture is cooled the solvents were removed under reduced pressure (water bath below 45° C.) The residue is cooled with an ice bath 3N NaOH solution was added The mixture is extracted with ether dried over MgSO4 The solvents were removed the residue is purified through a flash chromatographic column with a gradient of hexanes/ether