Trimethylsilyl iodide → 2,6-Dibromohydroquinone

Dissolve 2,6-dibromo-4-methoxyphenol (23.0 g, 80.6 mmol) in CH3CN (400 mL) and add trimethylsilyl iodide (TMSI) (53 mL, 371 mmol). Reflux the solution for 4 hours and add more TMSI (50 mL, 371 mmol). Heat the reaction at reflux overnight and cool to ambient temperature. Pour into ice-H2O (700 mL) and extract with EtOAc (2×300 mL). Wash the combined extracts with saturated sodium hydrosulfite (200 mL), H2O (200 mL) and brine (100 mL), dry over MgSO4, filter and concentrate. Crystallize the residue to provide the subtitled product (21.36 g, 98%) as a tan crystalline solid.

1. temperatureReflux the solution for 4 hours
2. temperatureHeat
3. customthe reaction
4. temperatureat reflux overnight
5. extractionextract with EtOAc (2×300 mL)
6. washWash the combined extracts with saturated sodium hydrosulfite (200 mL), H2O (200 mL) and brine (100 mL)
7. dry with materialdry over MgSO4
8. filtrationfilter
9. concentrationconcentrate
10. customCrystallize the residue

ORD record

ord-afadf83d216d4984b1d357d01498764b

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279499B2