Sodium Hydroxide → (R)-2-(4-chloro-3-fluorophenyl)oxirane

Participants

Reaction Steps

(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate (prepared as previously described in Example 1 (steps a-b) except substituting 1-(3-chloro-4-fluorophenyl)ethanone for 1-(4-fluoro-3-(trifluoromethyl)phenyl)ethanone, 3.35 g, 9.72 mmol) was dissolved in ether (80 mL) and 2N NaOH solution (25 mL) was added. The mixture was stirred at room temperature for 6 h until all starting material was consumed. The mixture was separated and the ether layer was washed with water. The organic layer was dried with sodium sulfate and solvents were removed to afford (R)-2-(4-chloro-3-fluorophenyl)oxirane as a colorless oil which was dried in vacuum (1.66 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.71-2.80 (m, 1H) 3.18 (dd, J=5.31, 4.04 Hz, 1H) 3.82-3.89 (m, 1H) 7.01-7.12 (m, 2H) 7.39 (dd, J=8.46, 7.45 Hz, 1H).

Provenance & Evidence