Reacción #56883

Ecuación de reacción

2-bromo-4-chloro-phenol

trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester

potassium carbonate

→

2-bromo-4-chloro-1-(2,2,2-trifluoro-ethoxy)-benzene

Rendimiento 108.0%

Disolventes

N,N-dimethylformaldehyde

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Concentraciónthe mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONThe residue was treated with water (150 ml)
4. 4
   Extracciónextracted with ethyl acetate (160 ml)
5. 5
   ExtracciónThe organic extract
6. 6
   Secadowas dried over magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4)

Procedimiento

A mixture of 2-bromo-4-chloro-phenol (2.0 g, 9.6 mmol), trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (3.8 g, 16.4 mmol), potassium carbonate (8.0 g, 59 mmol), and N,N-dimethylformaldehyde (80 ml) was heated to 100° C. for 72 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was treated with water (150 ml) and extracted with ethyl acetate (160 ml). The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4) to give 2-bromo-4-chloro-1-(2,2,2-trifluoro-ethoxy)-benzene (3.0 g, 100% yield). 1H NMR (acetone-d6) δ 4.80 (q, 2H, J=8.4 Hz, CH2), 7.28 (d, 1H, J=8.9 Hz, Ar), 7.45 (dd, 1H, J=8.9 Hz, J=2.5 Hz, Ar), 7.69 (d, 1H, J—2.5 Hz, Ar).

Fuente