Chemical Properties
Colorless to light yellow liqui
Uses
It is employed in biological research purpose. Benzyl bromoacetate was used in the alkylation of (-)-2,3-O-isopropylidene-D-threitol that afforded lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid.
Synthesis
General method: A mixture of acid 2 (0.033 g), 2-bromoacetic acid (3a) (0.137 g, 0.988 mmol) adsorbed on silica gel and benzyl alcohol (4a) (0.108 g, 1.000 mmol) was stirred and reacted at 80°C for 24 h under argon protection. After completion of the reaction, the mixture was cooled to room temperature, ether (5 mL x 5) was added for extraction, and the organic layer was separated by decantation from the silica gel adsorbed acid 2. The organic layer was concentrated under reduced pressure to remove the solvent, and then purified by silica gel column chromatography to afford benzyl 2-bromoacetate (5aa) (0.189 g, 83% yield) using hexane/ethyl acetate (v/v = 10/1) as eluent. The silica gel adsorbed acid 2 was recovered by vacuum drying at room temperature to give a white powder (0.033 g, 99% recovery).
Purification Methods
Dilute the ester with Et2O, wash it with 10% aqueous NaHCO3, H2O, dry (MgSO4) and fractionate it using a Fenske (glass helices packing) column. [Bergmann & Szinai J Chem Soc 1521 1956, Beilstein 6 IV 2265.] LACHRYMATORY.
References
[1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 367, p. 116 - 120
