Phosphorus tribromide → 2-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene

Participants

Role	Name	HCID	Charge
Reactant	Phosphorus tribromide	HCID 24614	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(4-Benzyloxy-2,6-dichloro-phenyl)methanol	HCID 66621751	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene	HCID 59299428	222.1%

Reaction Conditions

Temperature	0 °C

Reaction Steps

Treat a 0° C. solution of (2,6-dichloro-4-benzyloxy-phenyl)-methanol (247 g, 0.872 mol) in THF (2.5 L) with phosphorous tribromide (94.45 g, 0.35 mol) and stir for 30 minutes at 0° C. under N2. Pour the reaction into saturated NaHCO3 and extract twice with ethyl acetate. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford 269 g (89%) of the titled product. ES MS (m/z): 346 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968585B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-64f1d5381b1b446c9b7520322048f142
Source note	uspto-grants-2011_06