[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]=[C:7]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1.[OH-].[Na+]>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]To a solution of ethyl (5-fluoro-3,4-dihydronaphthalen-1-yl)acetate (16.4 g) in benzene (500 mL) was DDQ (2,3-dichloro-5,6-dicyanobenzoquinone)(21.5 g), and the mixture was stirred with heating for 3 hr. After cooling, the precipitated solid was dissolved in 1N sodium hydroxide, and the mixture was extracted with toluene. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give ethyl (5-fluoronaphthalen-1-yl)acetate (5.66 g).
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