N-[4-(hydroxymethyl)-2-iodophenyl]acetamide

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

Procedure: To a solution of IBX (0.93 g, 3.3 mmol) in dimethylsulfoxide (3.5 mL) was added N-(4-hydroxymethyl-2-iodo-phenyl)-acetamide (0.87 g, 3.0 mmol) and the reaction mixture was stirred at room temperature for 1 hour. Water (50 mL) was added and the solid was separated by filtration, and washed with ethyl acetate (20 mL). The filtrate was collected and extracted with ethyl acetate (200 mL). The organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. Removal of solvent gave N-(4-formyl-2-iodo-phenyl)-acetamide as a light brown solid. Yield: 0.82 g (95%). the solid was separated by filtration washed with ethyl acetate (20 mL) The filtrate was collected extracted with ethyl acetate (200 mL) The organic phase was washed with brine (100 mL) dried over anhydrous Na2SO4 Removal of solvent

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

Procedure: To a solution of IBX (0.93 g, 3.3 mmol) in dimethylsulfoxide (3.5 mL) was added N-(4-hydroxymethyl-2-iodo-phenyl)-acetamide (0.87 g, 3.0 mmol) and the reaction mixture was stirred at room temperature for 1 hour. Water (50 mL) was added and the solid was separated by filtration, and washed with ethyl acetate (20 mL). The filtrate was collected and extracted with ethyl acetate (200 mL). The organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. Removal of solvent gave N-(4-formyl-2-iodo-phenyl)-acetamide as a light brown solid. Yield: 0.82 g (95%). the solid was separated by filtration washed with ethyl acetate (20 mL) The filtrate was collected extracted with ethyl acetate (200 mL) The organic phase was washed with brine (100 mL) dried over anhydrous Na2SO4 Removal of solvent

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium aluminium hydride (2.43 g, 64.1 mmol) was taken in a dry, three-necked, round bottom flask. Anhydrous THF (80 mL) was added and cooled to −10° C. A solution of 4-acetylamino-3-iodo-benzoic acid methyl ester (10.2 g, 32.0 mmol) in anhydrous THF (60 mL) was added dropwise at −10° C. over a period of 45 minutes under nitrogen. Stirring was continued at −10° C. for 1 hour. The reaction mixture was quenched with saturated sodium sulfate aqueous solution. The reaction mixture was then filtered, and the filtrate was concentrated. The solid was washed with methanol. The combined organic phases were dried over anhydrous Na2SO4. The solvent was evaporated. The crude compound was purified by the Simpliflash system (5% methanol in CH2Cl2 as eluent), to give N-(4-hydroxymethyl-2-iodo-phenyl)-acetamide as a white solid. Yield: 6.36 g (68%). The reaction mixture was quenched with saturated sodium sulfate aqueous solution The reaction mixture was then filtered the filtrate was concentrated The solid was washed with methanol The combined organic phases were dried over anhydrous Na2SO4 The solvent was evaporated The crude compound was purified by the Simpliflash system (5% methanol in CH2Cl2 as eluent)

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

Procedure: To a solution of IBX (0.93 g, 3.3 mmol) in dimethylsulfoxide (3.5 mL) was added N-(4-hydroxymethyl-2-iodo-phenyl)-acetamide (0.87 g, 3.0 mmol) and the reaction mixture was stirred at room temperature for 1 hour. Water (50 mL) was added and the solid was separated by filtration, and washed with ethyl acetate (20 mL). The filtrate was collected and extracted with ethyl acetate (200 mL). The organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. Removal of solvent gave N-(4-formyl-2-iodo-phenyl)-acetamide as a light brown solid. Yield: 0.82 g (95%). the solid was separated by filtration washed with ethyl acetate (20 mL) The filtrate was collected extracted with ethyl acetate (200 mL) The organic phase was washed with brine (100 mL) dried over anhydrous Na2SO4 Removal of solvent

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium aluminium hydride (2.43 g, 64.1 mmol) was taken in a dry, three-necked, round bottom flask. Anhydrous THF (80 mL) was added and cooled to −10° C. A solution of 4-acetylamino-3-iodo-benzoic acid methyl ester (10.2 g, 32.0 mmol) in anhydrous THF (60 mL) was added dropwise at −10° C. over a period of 45 minutes under nitrogen. Stirring was continued at −10° C. for 1 hour. The reaction mixture was quenched with saturated sodium sulfate aqueous solution. The reaction mixture was then filtered, and the filtrate was concentrated. The solid was washed with methanol. The combined organic phases were dried over anhydrous Na2SO4. The solvent was evaporated. The crude compound was purified by the Simpliflash system (5% methanol in CH2Cl2 as eluent), to give N-(4-hydroxymethyl-2-iodo-phenyl)-acetamide as a white solid. Yield: 6.36 g (68%). The reaction mixture was quenched with saturated sodium sulfate aqueous solution The reaction mixture was then filtered the filtrate was concentrated The solid was washed with methanol The combined organic phases were dried over anhydrous Na2SO4 The solvent was evaporated The crude compound was purified by the Simpliflash system (5% methanol in CH2Cl2 as eluent)