Boron tribromide dichloromethane → HCID 68861328, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)isoindole-1,3-dione (29 g; 94.3 mmol) dissolved in anhydrous CH2Cl2 (500 mL), cooled to −60° C., is added a 1.0 M solution of boron tribromide-CH2Cl2 (471 mL), dropwise to maintain reaction temperature between −50 to −60° C. Upon completion of the addition, the reaction mixture is allowed to warm to RT and stirred for an additional 4 h. The reaction is cooled to 0° C., quenched with saturated NaHCO3 (400 mL) and stirred for an additional 0.5 h at RT. The precipitate is filtered, washed thoroughly with H2O, suspended in ether, filtered and dried under vacuo to afford 25.4 g (92%) of 2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)isoindole-1,3-dione as an off-white solid.

Provenance & Evidence