Sodium Cyanide → HCID 66678474, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2,4,5-trifluorobenzoate (DSL Chemicals; 950.61 mg; 5 mmol; 1 eq.), sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) and tetrabutylammonium bromide (2 014.82 mg; 6.25 mmol; 1.25 eq.) were dissolved in DMF (10 mL). The resulting mixture was heated at 60° C. overnight. As the reaction was not complete, sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) was added and the mixture was stirred at 60° C. for additional 24 h. The resulting dark pink solution was diluted with EtOAc and washed with brine several times. It was dried over MgSO4, filtrated and evaporated, resulting into a sticky dark red oil, which was purified by flash chromatography (SiO2 100 g, EtOAc/c-hex 1:9 until 1:1), affording the title product. 1H NMR (DMSO-d6, 300 MHz) δ 7.77 (dd, J=5.45, 8.41 Hz, 1H), 7.42 (dd, J=4.99, 8.88 Hz, 1H), 3.96 (s, 3H). LC/MS (Method A): 463.2 (M−H)−; 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).

Provenance & Evidence