Water → HCID 22329559, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of 2-bromo-5-fluoropyridine (1.88 g, 10.7 mmol), 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.13 g, 11.6 mmol) and potassium phosphate (8.2 g, 38.6 mmol) in 1,4-dioxane (40 ml) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloromethane adduct (189 mg) and the mixture stirred for 24 h at 90° C. The reaction was cooled to ambient temperature, poured into water (100 ml) and extracted with ethyl acetate (4×50 ml). The combined organic phases were dried over anhydrous sodium sulfate, filtered and evaporated to dryness. Purification by chromatography (silica gel, CH2Cl2) and then crystallisation from isohexane gave 5-fluoro-2-(2-fluoro-5-nitrophenyl)pyridine (1.23 g, 44%): MS (ES+) m/z 237.

Provenance & Evidence