5-Bromo-1-indanone → 5-bromo-2,3-dihydro-1H-inden-1-ol

Participants

Reaction Steps

Sodium borohydride (0.891 grams, 23.45 mmol) was added to a mixture of 5-bromo-indan-1-one (2.0g, 9.38 mmol)in MeOH (25 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 3 hours and quenched with saturated aqueous NH4Cl (25 mL) was added. The reaction mixture was diluted with EtOAc (200 mL). The organic layer was separated and was washed with saturated aqueous NaCl (3×50 mL), dried over sodium sulfate (Na2SO4) and concentrated in vacuo to yield 2.0 grams of a brown oil. 1H NMR (250 MHz, CDCl3): d 7.26 (m, 3 H), 5.18 (t, 1 H), 3.03 (m, 1 H), 2.80 (m, 1 H), 2.50 (m, 1 H), 193 (m, 1 H).

Provenance & Evidence