Carbon tetrabromide → tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (8.70 g, 33.1 mmol) and carbontetrabromide (17.0 g, 51.2 mmol) were added to a suspension of (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (7.00 g 31.2 mmol) in CH2Cl2 (200 mL) at room temperature. Stirring was continued for 5 h followed by evaporation of the solvent. Acetonitrile (200 mL) was added and the mixture was cooled to −20° C. for 2 h. The mixture was then filtered and the crystalline residue washed with cold acetonitrile (2×10 mL), to give (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (5.96 g, 67%).

Provenance & Evidence