Chloroiodomethane → 2-(2-(Trifluoromethyl)phenyl)oxirane

Temperature

-78 °C

α,α,α-trifluoro-o-tolualdehyde (3 g) was dissolved in anhydrous tetrahydrofuran and cooled to -78° C., iodochloromethane (1.38 ml) was then added, followed by methyllithium (1.5M complexed with lithium bromide) (12 ml) added over 5 minutes. The reaction was left to warm up to room temperature overnight. The reaction was quenched using saturated ammonium chloride solution and extracted using diethyl ether (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to afford a brown oil. Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane afforded a colourless oil (1.1 g). 1H NMR (250 MHz, CDCl3) δ2.61-2.71 (1H, dd), 3.14-3.25 (1H, dd), 4.17-4.27 (1H, m), 7.33-7.70 (5H, m).

1. additionadded over 5 minutes
2. waitThe reaction was left
3. temperatureto warm up to room temperature overnight
4. customThe reaction was quenched
5. extractionextracted
6. washThe combined organic extracts were washed with brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto afford a brown oil
10. customPurification on flash silica
11. washeluted with 100% hexane up to 5% EtOAC in hexane

ORD record

ord-622fcecd2a0b4607a07fac649d6051df

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728695