Chemical Properties
CLEAR COLORLESS LIQUID
Uses
2,4-Difluorobenzyl alcohol is used as pharmaceutical, pesticide, and liquid crystal material intermediates.
Synthesis
To a stirred solution of 2,4-difluorobenzaldehyde (500 mg, 3.52 mmol) in CH3OH (8 mL) was added NaBH4(266 mg, 7.04 mmol) portion wise at 0° C., and the reaction mixture was stirred at 0° C. for 1 h. After completion of the reaction (by TLC), CH3OH was removed under reduced pressure, diluted with ice-cold H2O (40 mL) and extracted with EtOAc (2.x.20 mL). The combined organic layers were washed with H2O (40 mL) and brine (40 mL), dried over anhydrous Na2SO4and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 10percent EtOAc/hexanes afforded 2,4-Difluorobenzyl alcohol (450 mg, 3.12 mmol, 88percent) as colorless liquid. 1H NMR (200 MHz, CDCl3): δ 7.45-7.33 (m, 1H), 6.83-6.75 (m, 2H), 4.72 (s, 2H), 1.79 (br s, OH).
References
[1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 564 - 576
[2] Organometallics, 2015, vol. 34, # 20, p. 5175 - 5182
[3] Patent: US2012/329788, 2012, A1. Location in patent: Page/Page column 26
[4] European Journal of Inorganic Chemistry, 2015, vol. 2015, # 16, p. 2732 - 2743
[5] Dalton Transactions, 2016, vol. 45, # 45, p. 18133 - 18141
