Methanol → 3-Iodo-7-methoxy-4H-1-benzopyran-4-one

Temperature

0 °C

To a solution of 3-(dimethylamino)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (20.0 g, 90.37 mmol) in anhydrous chloroform (100 ml) at 0° C. was added N-iodosuccinimide (23.5 g, 99.22 mmol) and silica gel (40 g). The reaction mixture was stirred at 0° C. for 60 minutes, then the insoluble material filtered off. The filtrate was washed with aqueous sodium thiosulfate (0.5M, 2×50 ml), followed by brine (100 ml), then dried over sodium sulfate. The solvent was removed under reduced pressure, providing an orange solid. To this solid was added methanol (30 ml), and the mixture was sonicated, filtered, the solid washed with methanol (2×5 ml), and the solid dried under reduced pressure, to give 3-iodo-7-methoxychromen-4-one as a pale yellow solid.

1. filtrationthe insoluble material filtered off
2. washThe filtrate was washed with aqueous sodium thiosulfate (0.5M, 2×50 ml)
3. dry with materialdried over sodium sulfate
4. customThe solvent was removed under reduced pressure
5. customproviding an orange solid
6. customthe mixture was sonicated
7. filtrationfiltered
8. washthe solid washed with methanol (2×5 ml)
9. customthe solid dried under reduced pressure

ORD record

ord-3ae1e58861c744f6b2d8dfd1e5d059e9

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158810B2