Hydrochloric Acid → HCID 57825221, compound

Temperature

-78 °C

To a solution of commercially available 1-bromo-4-ethoxy-benzene [588-96-5] (0.1 g, 25 mmol, 1.0 eq) in tetrahydrofuran (20 mL) was added dropwise a solution of n-butyllithium (1.6 M solution in hexane, 14.0 mL, 0.9 eq) at −78° C. After stirring 30 min at −78° C. 3-bromoacetophenone (3.7 mL, 1.1 eq) in tetrahydrofuran (20 mL) was added dropwise. The mixture was allowed to warm up to room temperature and stirred for 2 h, then treated with 1 N HCl (10 mL), extracted with ethyl acetate, dried (sodium sulfate) and concentrated in vacuo. The crude was dissolved in acetic acid (50 mL) and sulfuric acid (10 mL) and the mixture was warmed to 75° C. for 30 min, cooled to room temperature and 1 N NaOH was added up to pH=7. The aqueous phase was extracted with dichloromethane (3×10 mL), dried (sodium sulfate) the solvent was removed and the residue was purified by column chromatography (cyclohexane) to afford the title compound as a colorless oil (2.3 g, 30%);

1. temperatureto warm up to room temperature
2. stirringstirred for 2 h
3. extractionextracted with ethyl acetate
4. dry with materialdried (sodium sulfate)
5. concentrationconcentrated in vacuo
6. dissolutionThe crude was dissolved in acetic acid (50 mL)
7. temperaturesulfuric acid (10 mL) and the mixture was warmed to 75° C. for 30 min
8. temperaturecooled to room temperature
9. addition1 N NaOH was added up to pH=7
10. extractionThe aqueous phase was extracted with dichloromethane (3×10 mL)
11. dry with materialdried (sodium sulfate) the solvent
12. customwas removed
13. customthe residue was purified by column chromatography (cyclohexane)

ORD record

ord-7a150689009240b7b0861ae62b369172

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989449B2