1,3,5-Triiodo-2-methoxybenzene

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)

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

Procedure: In a 250 mL pressure vessel was added 2,4,6-triiodophenol (5 g, 10.60 mmol) in MTBE (60 ml) to give a yellow solution. The solution was cooled in an ice bath and 2.0M trimethylsilyldiazomethane (7.95 ml, 15.90 mmol) was added at a fast drip followed by dropwise addition of methanol (6 mL) resulting in calm bubbling. The vessel was sealed and stirred at room temperature for 4 h. The reaction solution was partitioned between EtOAc and water and the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl. The EtOAc was dried (MgSO4), filtered and concentrated to give a tan solid that was used without purification (4.8 g, 94%). to give a yellow solution The solution was cooled in an ice bath resulting in calm bubbling The vessel was sealed The reaction solution was partitioned between EtOAc and water the organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl The EtOAc was dried (MgSO4) filtered concentrated to give a tan solid that was used without purification (4.8 g, 94%)