Methyl iodide → HCID 89689483, compound

Participants

Reaction Conditions

Reaction Steps

683 mg (8.22 mmol) of 1-methyl-1,2,4-triazole in 20 ml of THF are admixed under argon at −78° C. with 3.3 ml (8.22 mmol) of butyllithium (2.5M, hexane). After 30 min, 1.22 g (8.63 mmol) of methyl iodide, dissolved in 2 ml of THF, are added, the cooling bath is removed and the mixture is left to reach RT. The mixture is cooled again to −78° C. and admixed with 3.3 ml (8.22 mmol) of butyllithium (2.5M, hexane). After 15 min, 1.22 g (4.12 mmol) of methyl 2-methyl-3-(methylsulfonyl)-4-trifluoromethylbenzoate are added and the mixture is left to thaw overnight. The mixture is quenched with ammonium chloride solution and extracted with EE. The organic phase is washed with NaHCO3 solution and NaCl solution, dried, evaporated and purified by means of RP-HPLC (acetonitrile/water). Yield 255 mg (17%). 1H NMR, CDCl3, 400 MHz: 7.90 (s, 1H), 7.82 (d, 1H), 7.72 (d, 1H), 5.57 (s, 1H), 3.85 (s, 3H), 3.27 (s, 3H), 2.84 (s, 3H).

Provenance & Evidence