Sulfuric Acid → 3-(2-Bromo-5-methoxy-phenyl)-1-phenyl-propan-1-one

To sodium ethoxide (5.72 g, 84 mmol) in 50 ml of anhydrous ethanol was added 14.8 g (77 mmol) of ethyl benzoylacetate with stirring. The reaction mixture was then brought to a gentle reflux and 19.6 g (70 mmol) of 1-Bromo-2-bromomethyl-4-methoxy-benzene in 20 ml of ethanol was added over 20 min. The reaction mixture was refluxed for 2 h. The reaction mixture was cooled, filtered and concentrated. The concentrated mixture was subjected to acid hydrolysis and decarboxylation by refluxing for overnight in a solution containing 40 ml of glacial acetic acid, 5 ml of concentrated sulfuric acid, and 10 ml of water. The reaction mixture was then neutralized with 10% NaOH and extracted with methylene chloride. The extracts were concentrated to give a weight of 19.43 g crude 3-(2-Bromo-5-methoxy-phenyl)-1-phenyl-propan-1-one (yield: 87%). This compound was used in next step without further purification.

1. temperaturea gentle reflux
2. temperatureThe reaction mixture was refluxed for 2 h
3. temperatureThe reaction mixture was cooled
4. filtrationfiltered
5. concentrationconcentrated
6. customThe concentrated mixture was subjected to acid hydrolysis and decarboxylation
7. temperatureby refluxing for overnight in a solution
8. extractionextracted with methylene chloride
9. concentrationThe extracts were concentrated

ORD-Eintrag

ord-381329a12af74001a30c9c130ea804a2

Quelldatensatz

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06323345B1