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

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).

1. temperatureThe reaction mixture was heated for 2 hours
2. temperatureunder reflux
3. customthe solvent was evaporated under reduced pressure
4. additionThe residue was treated with DCM
5. filtrationthe insoluble matter was filtered off
6. concentrationThe filtrate was concentrated in vacuo
7. dissolutionThe residue was dissolved in MeCN (10 mL)
8. customAfter concentration of the solution in vacuo, the residue was partitioned between AcOEt and H2O
9. extractionThe aqueous layer was extracted with AcOEt twice
10. washThe combined organic layers were washed with brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo

ORD record

ord-9d802dc30b1a4c1fb7523366f539f15c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018260B2