Triethylsilane → 6-bromo-4-fluoro-2,3-dihydro-1H-indene

To a solution of 6-bromo-4-fluoroindan-1-one (57 mg, 0.26 mmol) in trifluoroacetic acid (1.1 mL) was added triethylsilane (103 μL, 0.65 mmol), and the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was filtered through Phase-separator (Varian Inc.), and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0) to give a crude 6-bromo-4-fluoroindane (61 mg) as a yellow oil. The resultant was used in the next step without further purification. (2) The above crude product was treated in a similar manner to Reference example 41-(1) to give a crude methyl 7-fluoroindane-5-carboxylate. The resultant was used in the next step without further purification. (3) The above crude product was treated in a similar manner to Reference example 43-(2) to give a crude (7-fluoro-2,3-dihydro-1H-inden-5-yl)methanol. The resultant was used in the next step without further purification.

1. extractionthe mixture was extracted with ethyl acetate three times
2. washwashed with saturated aqueous sodium hydrogen carbonate solution
3. filtrationthe organic layer was filtered through Phase-separator (Varian Inc.)
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0)

ORD record

ord-10bc266e50664e968b56be33d33686ef

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987445B2