Sodium Bicarbonate → 3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol

Participants

Reaction Conditions

Reaction Steps

3-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (Example 132, 48 mg) was dissolved in 48% aqueous HBr (0.9 m) and stirred at 105° C. (bath temperature) for 4 h. The reaction mixture was then poured on ice-water-brine and sat aq NaHCO3 and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and evaporated in vacuo. The resulting brown residue was purified by flash chromatography (8 g silica gel, ethyl acetate/heptane 1:4) to give the title compound as off-white semisolid (34 mg). MS (m/e)=364.0 (M−H).

Provenance & Evidence