Boron tribromide → 5,6-Dihydroxy-2,3-dihydro-1H-inden-1-one

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Reaction Steps

To a solution of 5,6-dimethoxy-indan-1-one (40.0 g, 0.208 mol) in CH2Cl2 (800 mL) at −78° C. was added BBr3 (59.0 mL, 0.624 mol) dropwise. The dry ice bath was removed after the addition. The mixture was stirred at room temperature for 1 hour and poured into a large amount of ice/water and stirred vigorously. The pink solid was filtered, washed with water, and vacuum oven dried to give 33.3 g (98%) of the desired product. MS (DCI/NH3) m/z: 165.0 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 2.58-2.61 (m, 2H) 2.98 (t, J=5.55 Hz, 2H) 6.85 (s, 1H) 7.04 (s, 1H).

Provenance & Evidence