Tert-Butyl nitrite → 4,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,4-dibromo-6-(2,4-difluorophenyl)-5-methylpyridin-3-amine (10 g, 26.4 mmol, 1 eq) in THF (100 mL) was added tert-butylnitrite (4.7 mL, 39.6 mmol, 1.5 eq). The solution warmed and gas evolution was evident. After 2 h, the mixture was heated to and maintained at 60° C. for 45 min. The mixture was cooled and concentrated in vacuo. The product was purified by flash column chromatography eluting with 2% Et2O in hexanes to give 4,6-dibromo-2-(2,4-difluorophenyl)-3-methylpyridine. Mass spectrum (ESI) 362.2 (M+1); 364.2 (M+3); 366.2 (M+5).

Provenance & Evidence