Sodium borohydride → 4-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol

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Reaction Steps

Reaction under argon atmosphere: to a mixture of 1.69 g (43.7 mmol) of sodium borohydride in 120 ml isopropyl alcohol is added 20.0 g (87.3 mmol) of 4-bromo-7-fluoro-1-indanone portionwise. The reaction mixture is stirred at r.t. for 2 h. The solvent is evaporated. To the residue are added 100 g ice and 200 ml 1N aq. HCl. The mixture is extracted with EtOAc. The combined organic layers are washed with brine, dried and the solvent is evaporated. The residue is chromatographed on silica gel (PE/EtOAc=100/0→70/30) to give the title compound. Yield: 15.4 g; LC (method 4): tR=3.05 min; Mass spectrum (ESI+): m/z=213 [M+H—H2O]+.

Provenance & Evidence