Hydrogen Bromide → 3-Bromo-5-iodophenol

1-Bromo-3-iodo-5-methoxy-benzene (6.29 g, 20.1 mmol) was suspended in a solution of hydrogen bromide in acetic acid (33%, 150 mL). Tetrabutylammonium bromide (0.5 g, 1.55 mmol) was added and the mixture was heated to reflux under vigorous stirring for 2 d. After cooling to room temperature the mixture was extracted with methylene chloride (3×100 mL). The combined organic layers were washed with water (50 mL), dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9). 3-Bromo-5-iodo-phenol (21.2 g, 96%) was obtained as pale brown solid.

1. temperaturethe mixture was heated
2. temperatureto reflux
3. extractionwas extracted with methylene chloride (3×100 mL)
4. washThe combined organic layers were washed with water (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customto give the crude product which
8. customwas purified by flash chromatography on silica gel (300 g, AcOEt/heptane 1:9)

ORD record

ord-c82d30573024422aae1fd2c8d0f47fec

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504401B2