Triphenylphosphine → 3-Bromo-2-(2-but-1-ynyl-5-fluoro-phenoxymethyl)-pyridine

Participants

Reaction Steps

A solution of (3-bromo-pyridin-2-yl)-methanol (3.09 g, 16.43 mmol), 2-but-1-ynyl-5-fluoro-phenol (2.70 g, 16.43 mmol), and triphenylphosphine (6.46 g, 24.64 mmol) in dichloromethane (162 mL) is cooled to −5 to 0° C. Diisopropyl azodicarboxylate (DIAD) is added (4.85 mL, 24.64 mmol) dropwise over a 15 min period. After 1 h the solvent is evaporated and the crude material directly purified by flash chromatography (SiO2; 4% hexane: AcOEt) to give 3.5 g (64%) of the title compound. LCMS m/e 334 [M+H]+.

Provenance & Evidence