Water → 2,3,5-Triiodobenzyl mesylate

Temperature

0 °C

Mesyl chloride (0.6 ml, 8 mmol) was added dropwise to a suspension of 2,3,5-triiodobenzyl alcohol 1 (1.94 g, 4 mmol) in dry dichloromethane (30 ml) containing diisopropylethylamine (1.4 ml, 8 mmol) at 0° C. under dry nitrogen gas flow. The reaction mixture was stirred 1 h15 at 0° C., then cold H2O (40 ml) was added. The resulting aqueous phase was extracted with dichloromethane (10 ml). The combined organic extracts were washed with H2O (8 ml) then dried (Na2SO4), filtered and concentrated. The pale yellow solid was also washed with cold methanol (35 ml). 1.894 g of 2,3,5-triiodobenzyl mesylate in the form of a white clean solid was obtained in 84% yield.

1. extractionThe resulting aqueous phase was extracted with dichloromethane (10 ml)
2. washThe combined organic extracts were washed with H2O (8 ml)
3. dry with materialthen dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. washThe pale yellow solid was also washed with cold methanol (35 ml)

ORD record

ord-06f0003fb7f04460a0642a8020f29f7e

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434800B2