Water → 2,3,5-Triiodobenzyl mesylate
Reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[I:6][C:7]1[C:14]([I:15])=[CH:13][C:12]([I:16])=[CH:11][C:8]=1[CH2:9][OH:10].C(N(C(C)C)CC)(C)C.O>ClCCl>[S:1]([O:10][CH2:9][C:8]1[CH:11]=[C:12]([I:16])[CH:13]=[C:14]([I:15])[C:7]=1[I:6])(=[O:3])(=[O:2])[CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- extractionThe resulting aqueous phase was extracted with dichloromethane (10 ml)
- washThe combined organic extracts were washed with H2O (8 ml)
- dry with materialthen dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- washThe pale yellow solid was also washed with cold methanol (35 ml)
Sources & evidence
- ORD record
- ord-b3c177c46c9440bfbfacdcf93b922d39
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115230B2
Reaction notes
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