Ethanol → 3-(4-Bromophenyl)propionic acid

Sodium hydride (60% dispersion in oil; 4 g) was added portionwise to an ethanol (100 ml) solution of diethyl malonate (16 g) under ice-cooling. The reaction mixture was stirred at room temperature for 10 minutes, to which was added dropwise a THF (50 ml) solution of p-bromobenzylbromide (12 g) at room temperature. The reaction mixture was stirred at room temperature for 2 hours, and concentrated. Acetic acid (200 ml) and6N hydrochloric acid (100 ml) were added to the residue. The reaction mixture was stirred under heating at 90° C. for 18 hours, and concentrated. Water was added to the residue, which was extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1), which was recrystallized from IPE to obtain the entitled compound (1.2 g).

1. temperaturecooling
2. stirringThe reaction mixture was stirred at room temperature for 2 hours
3. concentrationconcentrated
4. additionhydrochloric acid (100 ml) were added to the residue
5. stirringThe reaction mixture was stirred
6. temperatureunder heating at 90° C. for 18 hours
7. concentrationconcentrated
8. additionWater was added to the residue, which
9. extractionwas extracted with ethyl acetate
10. washThe organic layer was washed with water
11. customdried
12. concentrationconcentrated
13. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1), which
14. customwas recrystallized from IPE

ORD record

ord-46f5a478a5a84dc9b9e6c53fe6a0d636

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329389B1