Potassium Carbonate → HCID 90456069, compound

Temperature

90 °C

A mixture of 3-iodo-5-(trifluoromethyl)phenol (5 g, 17.36 mmol, 1.00 equiv), 1-bromo-2-methoxyethane (3.6 g, 25.90 mmol, 1.49 equiv) and potassium carbonate (7.2 g, 52.09 mmol, 3.00 equiv) in N,N-dimethylformamide (50 mL) was stirred at 90° C. for 2 h. The resulting mixture was cooled to room temperature and diluted with water (50 mL). The mixture was extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 5.1 g (85%) of 1-iodo-3-(2-methoxyethoxy)-5-(trifluoromethyl)benzene as a yellow oil. 1H-NMR (300 MHz, DMSO-d6): δ 7.63-7.60 (m, 2H), 7.28 (s, 1H), 4.21-4.18 (m, 2H), 3.66-3.64 (m, 3H), 3.33 (s, 3H) ppm. LCMS (method D, ESI): RT=1.67 min.

1. temperatureThe resulting mixture was cooled to room temperature
2. extractionThe mixture was extracted with 3×50 mL of ethyl acetate
3. washThe combined organic layers were washed with 2×50 mL of brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under vacuum
6. customThe residue was purified on a silica gel column
7. washeluted with 0-20% of ethyl acetate in petroleum ether

ORD record

ord-24b595c5967c45aa83c81b993d8b4272

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952026B2