반응 #56883

반응 방정식

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

수율 108.0%

용매

N,N-dimethylformaldehyde

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   농축the mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONThe residue was treated with water (150 ml)
4. 4
   추출extracted with ethyl acetate (160 ml)
5. 5
   추출The organic extract
6. 6
   건조was dried over magnesium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4)

실험 절차

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).

출처