Methanol → 1,3,5-Triiodo-2-methoxybenzene

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%).

1. customto give a yellow solution
2. temperatureThe solution was cooled in an ice bath
3. customresulting in calm bubbling
4. customThe vessel was sealed
5. customThe reaction solution was partitioned between EtOAc and water
6. washthe organic layer was washed with 1M HCl, saturated NaHCO3, and saturated NaCl
7. dry with materialThe EtOAc was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a tan solid that
11. customwas used without purification (4.8 g, 94%)

ORD record

ord-33256af280ed491d82847c06164a0b33

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139536B2