Ethyl 7-bromoheptanoate

3.77 g of di-tert-butyl malonic acid was dissolved in 25 g of tert-butanol, and 1.96 g of potassium tert-butoxide and 2 g of 1,5-dibromopentane were added. The mixture was then heated to 45°C. 0.32 g of potassium tert-butoxide was added, and the mixture was stirred continuously for 1 hour. When the HPLC area percentage of di-tert-butyl malonic acid was less than 1%, 14 g of 10% aqueous acetic acid solution was added to remove the potassium tert-butoxide. 20 g of methyl tert-butyl ether was added to extract the resulting tetraester compound, and the organic layer was collected. This methyl tert-butyl ether layer was washed with 30 g of water, 30 g of 5% sodium bicarbonate aqueous solution, and 30 g of water. The water in the methyl tert-butyl ether layer was then removed with sodium sulfate. The sodium sulfate was removed by filtration, and the methyl tert-butyl ether was removed at 45°C. Finally, 3.11 g of ethyl 7-bromoheptanoate was obtained.

Figure 7. Synthetic Route of Ethyl 7-Bromoheptanoate

Colorless to pale yellow liquid

Ethyl 7-bromoheptanoate may be used in the following studies:

• As a starting material in the synthesis of benzyl 7-iodoheptanoate.
• As one of the reactant in the synthesis of diethyl 7,7′-(2,5-diiodo-1,4-phenylene)bis(oxy)diheptanoate.
• As one of the reagent in the synthesis of CarnDOD-7C, a carnitine-derived nitrone.
• As an alkylating agent in the alkylation of ethyl 3-oxoglutarate to form 2-(6-ethoxycarbonylhexyl)-3-oxoglutarate.
• Synthesis of 1-substituted cyclopentadiene by alkylating lithium cyclopentadienide.5

Ethyl 7-bromoheptanoate is a bromoester. It is used as an alkylating agent for organic compounds. It participates in the synthesis of ω-chain shortened prostaglandins.