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

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of diisopropylamine (14.35 mL, 0.102 mol) in 70 mL of THF was added n-BuLi (68 mL, 0.102 mol). The mixture was stirred at 0˜5° C. for 30 min. After the mixture was cooled to −78° C., ethyl isobutyrate (13.7 mL, 0.102 mol, 1 eq.) was added drop wise and stirring was maintained at −78° C. for 1 h. 1,3-Dibromopropane (1.01 equiv, 10.5 mL) was added drop wise at −78° C. and stirring was maintained at −78° C. for 1 h. Reaction was then warmed up to 23° C. over 2 hrs. Reaction mixture was added to an aqueous NH4Cl solution and extracted with EtOAc. The organic layer was washed with 1N HCl and brine, dried over MgSO4, filtered and concentrated down to give 23 g of crude product. The residue was purified by silica gel chromatography (5% to 30% EtOAc in hexanes) to provide 17.4 g (73% yield) of ethyl 5-bromo-2,2-dimethylpentanoate 90.

Provenance & Evidence