4-Bromoanisole → HCID 19431321, compound

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Reaction Steps

A small portion of 4-bromoanisole is added to a suspension of magnesium (72 mg, 3 mmol) in 6 ml of anhydrous THF. The mixture is heated at gentle reflux to initiate the reaction, then the remainder of the brominated derivative (0.56 g, 3 mmol), in solution in 5 ml of THF, is added dropwise over the course of 15 min. After reflux for 1 h, the magnesium has been consumed. 5,6-Dimethoxy-2,2-dimethylindan-1-one (0.66 g, 3 mmol) is added in small portions. The solution is stirred for 1 h at room temperature, then heated at reflux for 4 h. 10 ml of saturated aqueous NH4Cl solution are added at 0° C. The mixture is extracted with AcOEt. The organic phases collected are washed with saturated aqueous NaCl solution, dried over MgSO4 and evaporated to give a yellow oil (1.20 g). Purification by chromatography (eluent: AcOEt/hexane=1:5) enables the isolation of the expected product (0.65 g, 66%).

Provenance & Evidence