Description
Ethyl 4-bromobutyrate is a colourless volatile liquid organic or biological reagent. It is used in organic synthesis to prepare 4-bromobutyl ester, 4-bromobutyl amide and 4-bromobutyl ether. It is also used in the synthesis of poly(2,6-dimethyl-1,4-epoxyphenyl ether) and isotopic thieno[2,3-b]azepin-4-one thieno[2,3-b]-azepin-4-one with antitumour activity. In the biological field, it has been used in enzyme-linked immunosorbent assays for zilpaterol.
Chemical Properties
clear colorless to yellow liquid
Uses
A versatile building block and synthesis reagent
Uses
Ethyl 4-bromobutyrate is used as a building block for the preparation of firefly luciferase inhibitor-conjucated peptide derivatives. It finds application in the synthesis of poly(2,6,-dimethyl-1,4-phehylene oxide) and thieno(2,3-b)-azepin-4-ones.
Synthesis Reference(s)
The Journal of Organic Chemistry, 56, p. 2264, 1991
DOI: 10.1021/jo00006a061
Hazard
Strongly irritating to skin and eyes
Synthesis
Part A: Synthesis of ethyl 4-bromobutyrate
To a solution of 4-bromobutyric acid (3 g, 18 mmol) in ethanol (30 mL) was added 5 mL of a dioxane solution of 4N HCl. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the volatile components were removed under vacuum. The concentrated residue was dissolved in 150 mL of dichloromethane. The organic phase was washed sequentially with saturated aqueous NaHCO3 (1 x 150 mL) and brine (1 x 150 mL), dried over anhydrous MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The concentrated residue was dried under vacuum to give 3 g (85.5% yield) of ethyl 4-bromobutyrate as a yellow oil.1H NMR (300 MHz, CDCl3): δ1.22 (t, 3H, J = 7.15 Hz), 2.13 (m, 2H, J = 6.80 Hz), 2.45 (t, 2H, J = 7.15 Hz), 3.43 (t , 2H, J = 6.44Hz), 4.10 (q, 2H, J = 7.25Hz).
References
[1] Patent: US5753660, 1998, A
