Phosphorus tribromide → HCID 19861650, compound
Reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[C:7]([CH2:16]O)=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2>C(OCC)C>[Br:5][C:6]1[C:7]([CH2:16][Br:2])=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
PBr3 (3.7 mL, 0.039 mol) was added dropwise to a suspension of 3-bromo-2-naphthalenyl methanol (8.55 g, 0.036 mol) and diethyl ether (80 mL) at 0° C. After 1 hour, the reaction was concentrated and partitioned between CH2Cl2 and H2O. The organic layer was separated and dried over MgSO4. Concentration in vacuo afforded 3-bromo-2-bromomethylnaphthalene as a crude product (10.6 g). The crude product was flash chromatographed on silica gel to afford the pure product as an off-white powder (6.0 g, m.p. 110°-111° C., yield 56%).