Reaktion #1917239

Reaktionsgleichung

hydrochloric acid

4-iodo-5-chloro-2-methoxy benzoic acid

4-Iodo-5-chloro-2-methoxy benzoic acid

2-trifluoromethyl phenyl boronic acid

potassium carbonate

→

title acid

2-Chloro-2′-trifluoromethyl-5-methoxy-[1,1′-biphenyl]-4-carboxylic acid

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis mixture was purged with nitrogen
2. 2
   TemperaturThe reaction was heated
3. 3
   Temperaturto reflux overnight
4. 4
   Temperaturcooled
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed with brine
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated

Vorschrift

To a stirred solution of 4-iodo-5-chloro-2-methoxy benzoic acid of Step A (3.12 g, 10 mmol) in N,N-dimethylformamide(100 mL) was added 2-trifluoromethyl phenyl boronic acid (5.70 g, 30 mmol) and potassium carbonate (12.73 g, 92 mmol). This mixture was purged with nitrogen and then treated with a catalytic amount of tetrakis(triphenylphosphine) palladium(0) (0.58 g, 0.5 mmol). The reaction was heated to reflux overnight, cooled, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to provide a nearly quantitative amount of the title acid which was used in the next step without further purification.

Quelle