Potassium Carbonate → 2-Bromo-4-chloro-1-(2,2,2-trifluoroethoxy)-benzene

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).

1. temperatureAfter cooling to room temperature
2. concentrationthe mixture was concentrated under reduced pressure
3. additionThe residue was treated with water (150 ml)
4. extractionextracted with ethyl acetate (160 ml)
5. extractionThe organic extract
6. dry with materialwas dried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4)

ORD record

ord-5dfa535b15fa45bab30e6b895f399d6a

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07419984B2