Reaktion #90264

Reaktionsgleichung

2-(4′-(benzyloxy)-3′-methoxybiphenyl-3-yl)-6-(trifluoromethyl)pyridine

hydrogen bromide

acetic acid

→

3-methoxy-3′-(6-(trifluoromethyl)pyridin-2-yl)biphenyl-4-ol

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthen poured onto ice-water (100 mL)
2. 2
   SonstigeThe phases were separated
3. 3
   Extraktionthe aqueous phase was extracted with dichloromethane (10 mL)
4. 4
   WaschenThe combined organic layers were washed with water and brine
5. 5
   Trocknendried over anhydrous sodium sulphate
6. 6
   Filtrationfiltered
7. 7
   SonstigeEvaporation of the solvent
8. 8
   workup.WAITleft a brown oil that
9. 9
   Sonstigewas chromatographed over silica gel (petroleum ether/ethyl acetate, 4:1)

Vorschrift

To a solution of 2-(4′-(benzyloxy)-3′-methoxybiphenyl-3-yl)-6-(trifluoromethyl)pyridine (1.061 g, 2.44 mmol) in dichloromethane (20 mL) cooled in an ice-water bath was added a 30% solution of hydrogen bromide in acetic acid (4 mL, 20 mmol) dropwise. The resulting solution was allowed to stir at room temperature for six hours then poured onto ice-water (100 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (10 mL). The combined organic layers were washed with water and brine, then dried over anhydrous sodium sulphate and filtered. Evaporation of the solvent left a brown oil that was chromatographed over silica gel (petroleum ether/ethyl acetate, 4:1) to give 3-methoxy-3′-(6-(trifluoromethyl)pyridin-2-yl)biphenyl-4-ol as a clear oil, 0.547 g (65%).

Quelle