Chemical Properties
clear colorless to light yellow liquid
Uses
2,3-Difluorobenzyl bromide was used in the synthesis of chemokine antagonists.
Synthesis
Step 2 (MW-S2): phosphorus tribromide (6.7 mL, 69.44 mmol) was added dropwise to a solution of diethyl ether (250 mL) of 2,3-difluorobenzyl alcohol (20 g, 138.88 mmol) at -10 °C. The reaction mixture was stirred at -10 °C for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with diethyl ether (2 x 100 mL). The combined organic layers were washed sequentially with water (100 mL), brine (100 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum to give 20 g of 2,3-difluorobenzyl bromide (MW-52) as a light brown liquid, which can be used in the next reaction without further purification.
References
[1] Journal of Medicinal Chemistry, 1988, vol. 31, # 5, p. 1005 - 1009
[2] Patent: WO2014/140279, 2014, A1. Location in patent: Page/Page column 88; 170