4-(TRIFLUOROMETHYL)PHENETHYLALCOHOL

Borane dimethylsulfide complex (2M in THF, 6.9 ml, 13.8 mmol) was added slowly to a solution of the appropriate phenylacetic acid (10.6 mmol) in THF (20 ml) at room temperature. The reaction was stirred overnight before being quenched by the slow addition of sodium hydroxide (2N, 20ml). The mixture was stirred at room temperature for 1 h then extracted with ethyl acetate (2 x 50 ml). The organic layers were dried overMgS04 and condensed to give the appropriate alcohol as an oil (quantitative). Phosphorous tribromide (0.50 ml, 1.4 g, 5.3 mmol) was added to the neat alcohol whilst stirring in a room temperature water bath. The reaction was then heated to 100 C for 2 h until evolution of HBr ceased. The reaction was cooled and added dropwise to an ice/water mixture. The product was extracted twice with hexane and the combined organic layers washed with saturated sodium carbonate solution. The organic layer was dried A solution of Borane in tetrahydrofuran (1.0 M, 14.6 ml, 14.6 mmol) was added slowly to a solution of [4-(trifluoromethyl)phenyl]acetic acid (2.5 g, 11.3 mmol) in tetrahydrofuran (15 ml) in a water bath at room temperature. The reaction was stirred at room temperature for 16 h. The reaction was quenched by the addition of sodium hydroxide solution (2 M, 25 ml) and stirred for 1 h. The reaction was extracted with ethyl acetate (2 x 100 ml) and the organic layers dried over MgSOExample 60A Step i: 2-(4-(trifluoromethyl)phenyl)ethanol Part A: [0172] To a stirred mixture of LiAIH4 (950 mg, 0.25 mmol) in dry ether (40 mL) was added dropwise methyl 2-(4-(trifluoromethyl)phenyl)acetate (5.40 g 0.25mo1) in dry ether (10 mL) under ice-water bath cooling. The reaction mixture was stirred at ambient temperature for 2 hours and cautiously quenched by slow addition of water under ice-water bath cooling. The mixture was diluted with ethyl acetate and filtered through a pad of celite. After the filter mass was rinsed with ethyl acetate for several times, the organic phases were combined, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography over silica gel (ethyl acetate/hexane = 1/10) to afford the title compound as a colorless oil (4.50 g, 96percent). 1H NMR (400 MHz, CDCI3) 6 7.57 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 3.90 (t, J = 6.4 Hz, 2H), 2.93 (t, J = 6.4 Hz, 2H).4-Trifluoromethylphenyl ethanol: To a cooled solution of LAH in THF (1 M, 28 mL, 28 mmol) was added dropwise a solution of methyl 4-trifluoromethylphneyl acetate (5.97 g, 27 mmol) in THF (10 mL). The resulting mixture was stirred at room temperature for 2 hours, and then cooled in an ice bath. To this cooled mixture was added a saturated solution of NH(Second step)

Molecular Weight:190.16
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:190.06054939
Monoisotopic Mass:190.06054939
Topological Polar Surface Area:20.2
Heavy Atom Count:13
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes