Dichloromethane → HCID 53695021, compound

Participants

Reaction Steps

To a stirred suspension of (5-hydroxymethyl-3-vinyl-pyridin-2-yl)carbamic acid tert-butyl ester (10.0 g, 40.0 mmol) in CH2Cl2 (150 ml) and THF (60 ml) was added triphenylphosphine (11.5 g, 44.0 mmol) followed by carbontetrabromide (19.9 g, 60.0 mmol) at 0° C. The mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. Acetonitrile (100 ml) was added and the mixture was kept at −20° C. overnight. The mixture was then filtered and the crystalline residue washed with cold acetonitrile. The product was purified by flash-chromatography (1% MeOH in dichloromethane) to give (5-bromomethyl-3-chloro-pyridin-2-yl)-carbamic acid tert-butyl ester (4.5 g, 36%).

Provenance & Evidence