Carbon tetrabromide → 5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole

Participants

Role	Name	HCID	Charge
Reactant	Carbon tetrabromide	HCID 11205	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	[3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]methanol	HCID 66704107	—
Solvent	Dichloromethane	HCID 6344	—
Product	5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole	HCID 86629253	99.8%

Reaction Conditions

Temperature	0 °C

Reaction Steps

Triphenylphosphine (16.4 g, 62.5 mmol) is added to a suspension of [3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]-methanol (13 g, 41.69 mmol) in dichlormethane (80 mL). The mixture is cooled to 0° C. and carbon tetrabromide (20.7 g, 62.5 mmol) is added. The reaction is stirred at room temperature for 1.5 hours. The solvent is evaporated under reduced pressure and the residue is purified by flash chromatography eluting with hexanes/EtOAc (95:5 to 8:2) to obtain the title compound (15.6 g, 96% yield). ES/MS m/e 374 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08106077B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-c0597f6422ea4552934eb46de0b78687
Source note	uspto-grants-2012_01