Water → 1-(3-Bromo-5-hydroxyphenyl)ethanone

Temperature

110 °C

To a mixture of 1-(3-bromo-5-iodo-phenyl)-ethanone (2.28 g, 7.0 mmol), sodium hydroxide (1.4 g, 35.1 mmol), and Cu2O (143 mg, 1.0 mmol) were added pyridine (20 mL) and water (40 mL) at room temperature. The resulting suspension was heated to 110° C. and stirred for 24 h. Then the reaction mixture was cooled to room temperature and diluted with 1N hydrochloric acid (200 mL). Then, the organic compound was extracted into ethyl acetate (3×100 mL) and the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which was tried to dissolve in acetonitrile (50 mL) at reflux, but it did not dissolve completely. Then, it was diluted with ethyl acetate (˜10 mL) and hexanes (˜15 mL). The dark suspension was stored in the refrigerator. Only few solids were formed and they were coolected by filtration and washed with acetonitrile. Then, the mother liquor was removed under vacuum and the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux and it was treated with charcoal to remove some color. It was then filtered and the solvent was removed under vacuum to afford reasonably pure 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 64%) as a brown solid: ES(−)-HRMS m/e calcd for C8H7BrO2 (M−H)− 212.9556. found 212.9556.

1. temperatureThen the reaction mixture was cooled to room temperature
2. extractionThen, the organic compound was extracted into ethyl acetate (3×100 mL)
3. washthe combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL)
4. dry with materialThe organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum
5. customgave the crude dark brown solid which
6. temperatureat reflux
7. dissolutionit did not dissolve completely
8. customOnly few solids were formed
9. filtrationthey were coolected by filtration
10. washwashed with acetonitrile
11. customThen, the mother liquor was removed under vacuum
12. dissolutionthe dark brown solids were now dissolved in acetonitrile (50 mL)
13. temperatureat reflux
14. additionit was treated with charcoal
15. customto remove some color
16. filtrationIt was then filtered
17. customthe solvent was removed under vacuum

ORD record

ord-a20decf6950e40eeb1551b762feda15b

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088936B2