Iodine → 5-fluoro-6-hydroxy-7-iodobenzofuran-3(2H)-one

HRID 1750006Notes

Reaction equation

HRID 1750006 reaction equation
[F:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=1.II.[I:15](O)(=O)=O>C(O)C.O>[F:1][C:2]1[C:3]([OH:12])=[C:4]([I:15])[C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=1

Participants

6

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 574435465-fluoro-6-hydroxybenzofuran-3(2H)-one

Product 1

HCID 712785875-fluoro-6-hydroxy-7-iodobenzofuran-3(2H)-oneYield 385.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 5-fluoro-6-hydroxybenzofuran-3(2H)-one (0.190 g, 1.13 mmol) in ethanol (5 mL) was added with iodine (0.115 g, 0.452 mmol) at room temperature. The reaction mixture was added dropwise with a solution of iodic acid (0.0396 g, 0.226 mmol) in water (2 mL), and the mixture was stirred for 2 hours. The reaction mixture was added with water (30 mL), and the precipitated solid was collected by filtration, and dried under reduced pressure to obtain 5-fluoro-6-hydroxy-7-iodobenzofuran-3(2H)-one (0.256 g, 77%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-0af3daa30f1b4cfbac35980cd8872441
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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