(4'-TRIFLUOROMETHYLBIPHENYL-4-YL)-METHANOL Chemical Properties

Melting point:

147-149°

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

Safety Information

HazardClass 

IRRITANT

(4'-TRIFLUOROMETHYLBIPHENYL-4-YL)-METHANOL Usage And Synthesis

Synthesis

LiAlH4 (2.0 M THF solution, 3.0 mL, 6.00 mmol) was dissolved in anhydrous THF (10 mL) under nitrogen protection and cooled to 0 °C. To this stirred mixture was added dropwise a solution of 4'-[4-(trifluoromethyl)phenyl]benzoic acid (0.4 g, 1.5 mmol) in anhydrous THF (10 mL). The reaction mixture was stirred at room temperature for 4 hours. Subsequently, H2O (0.23 mL), 3.0 M KOH solution (0.23 mL) and H2O (0.77 mL) were added slowly at 0 °C. The mixture was continued to be stirred at 0 °C for 1 h. The solid residue was removed by filtration and the organic phase was dried with Na2SO4. The organic solution was filtered again and concentrated to dryness. The crude product was purified by column chromatography using a Teledyne ISCO unit with the eluent cyclohexane/ethyl acetate (100:0 to 70:30) to afford 4'-trifluoromethyl-4-biphenylmethanol (0.3 g, 79%) as a white solid.1H NMR (DMSO-d6) data were as follows: δ 4.56 (d, J=5.7 Hz, 2H), δ 5.25 (t, J=5.7Hz, 1H), 7.45 (d, J=8.1Hz, 2H), 7.70 (d, J=8.1Hz, 2H), 7.81 (d, J=8.1Hz, 2H), 7.89 (d, J=8.1Hz, 2H).

References

[1] Patent: WO2013/78430, 2013, A1. Location in patent: Paragraph 0353
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 23, p. 10101 - 10111
[3] Patent: US9353075, 2016, B2. Location in patent: Page/Page column 122
[4] Patent: WO2009/71504, 2009, A1. Location in patent: Page/Page column 65
[5] Patent: WO2010/15653, 2010, A1. Location in patent: Page/Page column 39

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