N-Iodosuccinimide → 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one

HRID 1502036Notes

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]=1

Participants

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 with EtOAc (3×500 mL) and the combined organic layers were washed with saturated NaHCO3 solution and brine, and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica column chromatography (EtOAc/Petrol Ether=1:5) to give 5-(2-hydroxyethyl)-6-iodo-2-benzofuran-1(3H)-one and its separated regioisomer.

Workup

extractionThe solution was extracted with EtOAc (3×500 mL)
washthe combined organic layers were washed with saturated NaHCO3 solution and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica column chromatography (EtOAc/Petrol Ether=1:5)

Sources & evidence

ORD record: ord-e1e94ac955e5420092a94df7bf98fde7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206199B2

Reaction notes

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