Reaction #1973968

Reaction equation

2,4,6-triiodophenol

trimethylsilyldiazomethane

methanol

→

1,3,5-triiodo-2-methoxybenzene

Solvents

MTBE

Conditions

Workup

1. 1
   Otherto give a yellow solution
2. 2
   TemperatureThe solution was cooled in an ice bath
3. 3
   Otherresulting in calm bubbling
4. 4
   OtherThe vessel was sealed
5. 5
   OtherThe reaction solution was partitioned between EtOAc and water
6. 6
   Washthe organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl
7. 7
   DryingThe EtOAc was dried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated
10. 10
    Otherto give a tan solid that
11. 11
    Otherwas used without purification (4.8 g, 94%)

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%).

Source