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With pyridinium chlorochromate In diethyl ether; dichloromethane for 3 h;
Dissolve (5-chloro-2-trifluoromethylphenyl)-methanol (347 mg, 1.66 mmol) in dichloromethane (10 mL). Add pyridinium chlorochromate (717 mg, 3.32 mmol) and stir for 2 h. Dilute with diethyl ether and stir for 1 h. Filter and concentrate. Chromatograph on silica gel eluting with 10percent ethyl acetate in hexane to give the title compound as a clear EPO <DP n="15"/>oil (285 mg, 82percent). 1HNMR (400 MHz, MeOH-d4) δ 10.33 (s, IH), 7.90 (s, IH), 7.69 (d, IH5 J = 8.4 Hz), 7.54 (d, IH, J = 8.4 Hz).
Add borane-THF complex (3.34 mL, 3.34 mmol) slowly to an ice-methanol cooled bath solution of 5-chloro-2-trifluoromethyl-benzoic acid (500 mg, 2.23 mmol) in THF (2 mL). Stir overnight at room temperature. Add water (1 mL) and solid potassium carbonate. Filter and concentrate to give an oil residue. Chromatograph on silica gel, eluting with 10:90 to 1:1 ethyl acetate :hexanes to give (5-chloro-2- trifluoromethylrhohenyl)-methanol as a white solid (347 mg, 75%). 1H NMR (400 MHz, MeOH-d4) delta 7.84 (s, IH), 7.68 (d, IH5 J = 8.4 Hz)5 7.48 (d, IH, J = 8.4 Hz), 4.81 (s, 2H).
With pyridinium chlorochromate; In diethyl ether; dichloromethane; for 3.0h;
Dissolve <strong>[261763-21-7](5-chloro-2-trifluoromethylphenyl)-methanol</strong> (347 mg, 1.66 mmol) in dichloromethane (10 mL). Add pyridinium chlorochromate (717 mg, 3.32 mmol) and stir for 2 h. Dilute with diethyl ether and stir for 1 h. Filter and concentrate. Chromatograph on silica gel eluting with 10% ethyl acetate in hexane to give the title compound as a clear EPO <DP n="15"/>oil (285 mg, 82%). 1HNMR (400 MHz, MeOH-d4) delta 10.33 (s, IH), 7.90 (s, IH), 7.69 (d, IH5 J = 8.4 Hz), 7.54 (d, IH, J = 8.4 Hz).
5-chloro-2-(trifluoromethyl)benzyl methanesulfonate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In dichloromethane; at 0℃; for 1.0h;
To a solution of(5-chloro-2- (trifluoromethyl)phenyl)methanol (400 mg, 1.90 mmol)and triethylamine (0.794 mL, 5.70mmol) in DCM (8 mL) was added methanesulfonyl chloride (0.148 mL, 1.90 mmol) at 0C. The reaction was stirred for 1 hour at 0 C, then quenched with water (10 mL) and extracted with DCM (10 mL x 3). The combined organic layers were washed with brine (saturated, 10 mL), dried over Mg504 and filtered. The filtrate was concentrated under reduced pressure to give the title compound, which was used in the next step without purification.
With methanol; sodium tetrahydroborate; at 0 - 25℃; for 1.0h;
To a solution of 5-chloro-2- (trifluoromethyl)benzaldehyde (500 mg, 2.40 mmol) in MeOH (5 mL) was added NaBH4 (182 mg, 4.80 mmol) at 0C. The reaction was stirred at 25 C for 1 hour, then quenched with water (3 mL) and extracted with EtOAc (5 mL x 3). The combined organic layers were washed with brine (saturated, 5 mL), dried over Mg504 and filtered. The filtrate wasconcentrated under reduced pressure to give the title compound, which was used in the next step without purification. 1H NMR (400MHz, CDC13): oe = 7.77 (s, 1H), 7.58 (d, J= 8.2 Hz, 1H), 7.37 (d, J= 8.2 Hz, 1H), 4.89 (s, 2H)
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