7-methyl-2,3-dihydro-1H-inden-1-one → 2-Fluoro-7-methyl-2,3-dihydro-1H-inden-1-one

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Reaction Steps

To a solution of 7-methyl-1-indanone (CAS No. 39627-61-7,513 mg, 3.51 mmol) in MeOH (18 mL) was added Selectfluor™ (1.49 g, 4.21 mmol) at room temperature. The reaction mixture was heated for 2 hours under reflux. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was treated with DCM and the insoluble matter was filtered off. The filtrate was concentrated in vacuo. The residue was dissolved in MeCN (10 mL) and 5 N HCl (5 mL). The solution was stirred at room temperature for 30 mins. After concentration of the solution in vacuo, the residue was partitioned between AcOEt and H2O. The aqueous layer was extracted with AcOEt twice. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (555 mg, 3.38 mmol).

Provenance & Evidence