Reacción #164954

Ecuación de reacción

5-Amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester

CF3COOH

PPh3

NEt3

CCl4

→

5-[1-chloro-2,2,2-trifluoro-eth-(Z)-ylideneamino]-4′-methyl-biphenyl-3-carboxylic acid methyl ester

Rendimiento 60.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturato reflux for 2 hours
3. 3
   OtroSolvent was removed under reduced pressure
4. 4
   Otrothe residue was purified by flash column chromatography
5. 5
   Lavadoeluting with n-hexane:ethyl acetate (10:1)

Procedimiento

A mixture of CF3COOH (5.19 mmol, 398 mL), PPh3 (15.56 mmol, 4.08 g) and NEt3 (6.22 mmol, 868 μL) in 10 mL of CCl4 was stirred at 0° C. for 10 minutes. 5-Amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (1.5 g, 6.22 mmol) was then added to the reaction mixture and the mixture was heated to reflux for 2 hours. Solvent was removed under reduced pressure and the residue was purified by flash column chromatography, eluting with n-hexane:ethyl acetate (10:1), giving the 5-[1-chloro-2,2,2-trifluoro-eth-(Z)-ylideneamino]-4′-methyl-biphenyl-3-carboxylic acid methyl ester as light yellow oil (1.3 g, 60% yield).

Fuente