Reaktion #1917242

Reaktionsgleichung

hydrochloric acid

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

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

2-chloro phenyl boronic acid

potassium carbonate

→

title acid

Ausbeute 74.8%

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

Ausbeute 74.8%

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 Example 5, Step A (3.38 g, 10.8 mmol) in N,N-dimethylformamide (80 mL) was added 2-chloro phenyl boronic acid (5.07 g, 32.4 mmol) and potassium carbonate (3.44 g, 32.4 mmol). This mixture was purged with nitrogen and then treated with tetrakis(triphenylphosphine) palladium(0) (0.625 g, 0.54 mmol). The reaction was heated to reflux overnight, cooled, acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to provide 2.4 g of the title acid which was used in the next step without further purification.

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