Carbon tetrabromide → 3-Bromo-5-(bromomethyl)pyridine

Participants

Role	Name	HCID	Charge
Reactant	Carbon tetrabromide	HCID 11205	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	(5-Bromo-3-pyridinyl)methanol	HCID 2784733	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-Bromo-5-(bromomethyl)pyridine	HCID 14932948	91.4%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a cooled (0° C.) solution of (5-bromo-pyridin-3-yl)-methanol (5.0 g, 26.6 mmol) and triphenylphosphine (8.4 g, 31.9 mmol) in DCM (130 mL) is added carbon tetrabromide (13.2 g, 39.9 mmol). The resulting mixture is stirred at 0° C. for 10 min. The mixture is concentrated and purified by silica gel column (0-40% EtOAc in heptane) to afford the title compound (6.1 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181272B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-5a60ea52cee24a2ba758cba0fb909228
Source note	uspto-grants-2015_11