N-Iodosuccinimide → 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one
Reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.C1C(=O)N([I:21])C(=O)C1>S(O)(C(F)(F)F)(=O)=O>[OH:1][CH2:2][CH2:3][C:4]1[C:13]([I:21])=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of 5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one (9.00 g, 50.6 mmol) in 100 mL of TfOH was added NIS (12.5 g, 55.6 mmol), then the mixture was stirred at 0° C. for 2 hrs and then poured into ice-water (500 mL). The solution was extracted three times with 500 mL of EtOAc and the combined organic layers were washed with saturated NaHCO3 and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (EtOAc/Petrol Ether=1:5) to give the desired 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one (6 g) and isomeric by-product 5-(2-hydroxyethyl)-4-iodo-2-benzofuran-1(3H)-one.
Workup
- extractionThe solution was extracted three times with 500 mL of EtOAc
- washthe combined organic layers were washed with saturated NaHCO3 and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography (EtOAc/Petrol Ether=1:5)
Sources & evidence
- ORD record
- ord-724d09525fd548c3ace373ae03b6f95a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673920B2
Reaction notes
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