Potassium Carbonate → HCID 43805642, compound

1-[5-Bromo-2-hydroxyphenyl]ethanone (13.4 g) was dissolved in N,N-dimethylformamide (300 mL). To the reaction mixture were added potassium carbonate (25.8 g) and 2-bromo-1-cyclohexylethanone (19.0 g) synthesized in Example A51(1) at room temperature, and the mixture was stirred for 3 hr. The reaction mixture was filtered through celite, water (200 mL) was added, and the mixture was extracted with diethyl ether (100 mL×2). The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (150 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (9.3 mL) was added to the solution at room temperature, and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was allowed to cool to room temperature, 1N hydrochloric acid (70 mL) was added, and the mixture was extracted with diethyl ether (100 mL×2). The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The precipitate was washed with diisopropyl ether to give the title object compound (15.4 g, 77%) as a pale-yellow solid.

1. customsynthesized in Example A51(1) at room temperature
2. filtrationThe reaction mixture was filtered through celite, water (200 mL)
3. additionwas added
4. extractionthe mixture was extracted with diethyl ether (100 mL×2)
5. washThe extract was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. dissolutionThe residue was dissolved in N,N-dimethylformamide (150 mL)
9. addition1,8-diazabicyclo[5.4.0]undec-7-ene (9.3 mL) was added to the solution at room temperature
10. stirringthe mixture was stirred at 100° C. for 1 hr
11. addition1N hydrochloric acid (70 mL) was added
12. extractionthe mixture was extracted with diethyl ether (100 mL×2)
13. washThe extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
14. dry with materialdried over magnesium sulfate
15. concentrationconcentrated under reduced pressure
16. washThe precipitate was washed with diisopropyl ether

ORD record

ord-f2106312ba8740e0899390cb36c18cec

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2