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 being stirred, 126 ml of a 1.6 M solution of n-butyl lithium in hexane wasadded at -5° to 0° C., followed by stirring for 30 minutes. After the reaction mixture was cooled to -78° C. and 26.7 ml of ethyl isobutyrate was added dropwise to the mixture and stirred for 1 hour. 41.8 g of 1,3-dibromopropane was added dropwise to the reaction mixture. After stirring at -78° C. for 1 hour and then at room temperature (15° to 20° C.) for 2 hours, the reaction mixture was added to an aqueous solution of ammonium chloride and extracted with ethyl acetate. After the extract was washed with water and dried, the solvent was distilled off, and the residue was distilled under reduced pressure, to yield 40.3 g of the title compound in the form of a colorless oily substance.

1. customwasadded at -5° to 0° C.
2. stirringstirred for 1 hour
3. stirringAfter stirring at -78° C. for 1 hour
4. waitat room temperature (15° to 20° C.) for 2 hours
5. extractionextracted with ethyl acetate
6. washAfter the extract was washed with water
7. customdried
8. distillationthe solvent was distilled off
9. distillationthe residue was distilled under reduced pressure

ORD record

ord-e504768dc0314259aa996e39fb8e65a7

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05491145