Ethyl isobutyrate → Ethyl 5-bromo-2,2-dimethylpentanoate

Temperature

-78 °C

To a solution of 28.7 ml of diisopropylamine in 150 ml of tetrahydrofuran was added 126 ml of 1.6M n-butyllithium-hexane with stirring at -5° to 0° C. and the mixture was further stirred for 30 minutes. This reaction mixture was cooled to -78° C. and 26.7 ml of ethyl isobutyrate was added dropwise. The mixture was stirred for 1 hour, after which 41.8 g of 1,3-dibromopropane was added dropwise. The reaction mixture was stirred at -78° C. for 1 hour and then at room temperature for 2 hours. The mixture was then poured in aqueous solution of ammonium chloride and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was then distilled off and the residue was subjected to vacuum distillation to provide 40.3 g of the title compound as colorless oil. b.p. 76°-78° C./0.27 mmHg

1. stirringthe mixture was further stirred for 30 minutes
2. stirringThe mixture was stirred for 1 hour
3. stirringThe reaction mixture was stirred at -78° C. for 1 hour
4. extractionextracted with ethyl acetate
5. washThe extract was washed with water
6. customdried
7. distillationThe solvent was then distilled off
8. distillationthe residue was subjected to vacuum distillation

ORD record

ord-558fbefad2c5429a98e091c931c1bd15

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05389633