Sodium Hydroxide → 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol

Temperature

25 °C

To a stirred solution of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone (procured from Rieke Metals, UK; 5.0 grams (g), 20.5 millimoles (mmol)) in methyl alcohol (CH3OH; 100 milliliters (mL)) at 0° C. were added sodium borohydride (NaBH4; 3.33 g, 92.5 mL) and 1 Normal (N) aqueous sodium hydroxide solution (NaOH; 10 mL). The reaction mixture was warmed to 25° C. and stirred for 2 hours (h). After the reaction was deemed complete by thin layer chromatography (TLC), saturated (satd) aqueous (aq) ammonium chloride (NH4Cl) solution was added to the reaction mixture, and the mixture was concentrated under reduced pressure. The residue was diluted with diethyl ether (Et2O) and washed with water (H2O; 3×50 mL). The organic layer was dried over sodium sulfate (Na2SO4) and concentrated under reduced pressure to afford the title compound as a liquid (4.0 g, 79%): 1H NMR (400 MHz, CDCl3) δ 7.41 (m, 3H), 5.00 (m, 2H), 2.74 (s, 1H); ESIMS m/z 242.97 ([M−H]−).

1. additionwas added to the reaction mixture
2. concentrationthe mixture was concentrated under reduced pressure
3. additionThe residue was diluted with diethyl ether (Et2O)
4. washwashed with water (H2O; 3×50 mL)
5. dry with materialThe organic layer was dried over sodium sulfate (Na2SO4)
6. concentrationconcentrated under reduced pressure

ORD record

ord-9ded0283348e464d9856209e15dedac0

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212164B2