(3-CHLORO-5-(TRIFLUOROMETHOXY)PHENYL)METHANOL synthesis

Yield:433926-47-7 100%

Reaction Conditions:

Stage #1: 3-chloro-5-(trifluoromethoxy)benzoic acidwith borane-THF in tetrahydrofuran at 20; for 20 h;Heating / reflux;
Stage #2: with water in tetrahydrofuran;

Steps:

6.v (v) 3-Chloro-5-trifluoromethoxybenzyl alcohol

To a solution of 3-chloro-5-trifluoromethoxybenzoic acid (22.5 g, 93.5 mmol; see step (iv) above) in anhydrous THF (1200 mL) under a N₂ atmosphere at room temperature was added a solution of BH₃.THF complex (140 mL of 1M in THF; 140.3 mmol). The solution was refluxed for 2 h, cooled to room temperature and stirred for 18 hours, quenched cautiously with H₂O and concentrated in vacuo to remove most of the THF. The residue was diluted with EtOAc and the organics were washed with brine (3*), dried (Na₂SO₄), filtered and concentrated in vacuo to give the crude sub-title compound (21.2 g, 100%) as an oil that was used without further purification. ¹H NMR (300 MHz, CDCl₃): δ7.33 (s, 1H), 7.17 (s, 1H), 7.14 (s, 1H), 4.72 (s, 2H), 2.05 (br s, 1H)

References:

US2004/19033,2004,A1 Location in patent:Page/Page column 19