Phosphorus tribromide → 2-Bromomethyl-3-methylnaphthalene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-hydroxymethyl-3-methylnaphthalene (2.47 g, 14.4 mmol) in dry Et2O (50 mL) cooled to 0° C. was added phosphorus tribromide (4.88 g, 18 mmol) dropwise over 20 minutes. The resulting heterogeneous mixture was stirred at 0° C. for 1.25 hours and then quenched with H2O (50 mL). The reaction mixture was diluted further with H2O (50 mL) and extracted with Et1O (2×150 mL). The combined organic layers were washed with H2O (1×100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by filtration through silica gel using CH2Cl2 as eluent to give the product as an off-white solid (2.94 g, 87%).

Provenance & Evidence