2-(3-FLUORO-5-(TRIFLUOROMETHYL)PHENYL)ETHANOL synthesis

Yield:955036-77-8 100%

Reaction Conditions:

Stage #1: methyl 2-(3-fluoro-5-(trifluoromethyl)phenyl)acetatewith diisobutylaluminium hydride in hexane;toluene at 20; for 1.5 h;
Stage #2: with hydrogenchloride;methanol;water in hexane;toluene at 0;

Steps:

3

3-Fluoro-5-trifluoromethylphenyl ethanol: To cooled solution of methyl 3-fluoro-5-trifluoromethylphenyl acetate (6.54 g, 27.7 mmol) in hexane (30 mL) was added a solution of DIBAL in toluene (1.5 M, 40 mL, 60 mmol). The cooling bath was removed. The reaction mixture was stirred at room temperature for 90 min. The reaction mixture was cooled in an ice bath, and MeOH (55 mL) was added, followed by aqueous HCl (6 N, 11 mL). The resulting mixture was extracted with ether (2×30 mL). The combined ether layers were washed with brine (20 mL), dried (Na₂SO₄), filtered, and concentrated to give the product (5.7 g, 100%). 1H NMR (CDCl₃, 300 MHz) d 2.93 (t, J=6.4 Hz, 2H), 3.91 (t, J=6.4 Hz, 2H),7.12-7.35 (m, 3H).

References:

US2007/293548,2007,A1 Location in patent:Page/Page column 59