Hydrogen Peroxide → 2-Fluoro-5-iodophenol

To a cooled solution of 2-fluoro-5-iodophenylboronic acid in tetrahydrofuran (200 mL) at 0° C. add an aqueous solution of 30% hydrogen peroxide (9.92 mL, 103 mmol) dropwise, stir 10 min, and add an aqueous 4 N solution of sodium hydroxide (1.78 mL, 7.12 mmol). Warm the reaction to room temperature and stir overnight. Add manganese dioxide (250 mg) to the reaction, stir 90 min and filter through fluted filter paper. Concentrate and partition the residue between diethyl ether and water. Separate the layers and sequentially wash the organic layer with water and an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter and concentrate. Purify the resulting tan oil by silica gel chromatography, eluting with a gradient of 0:100 to 30:70 ethyl acetate:hexanes, to give the title compound as a yellow waxy solid (18.1 g, 65%).

1. temperatureWarm
2. customthe reaction to room temperature
3. stirringstir overnight
4. stirringstir 90 min
5. filtrationfilter
6. filtrationthrough fluted filter paper
7. concentrationConcentrate
8. custompartition the residue between diethyl ether and water
9. customSeparate the layers
10. washsequentially wash the organic layer with water
11. dry with materialDry (sodium sulfate)
12. filtrationfilter
13. concentrationconcentrate
14. customPurify the resulting tan oil by silica gel chromatography
15. washeluting with a gradient of 0:100 to 30:70 ethyl acetate

ORD record

ord-85b8cbf127b34f26b6a74e6cd07837fc

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915424B2