[C:1]12([OH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[H][H].[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F>O.CN(C)C=O.C1C=CC=CC=1>[C:1]12([O:11][C:22]3[CH:21]=[CH:20][C:19]([N+:24]([O-:26])=[O:25])=[CH:18][C:17]=3[F:16])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2
A mixture of 16 g (64 mmoles) of 1-adamantanol, 3.35 g (70 mmoles NaH) of 50% NaH in oil, 60 ml of benzene, and 60 ml of dimethylformamide is heated until hydrogen is vigorously evolved (80°). Heating is discontinued until the effervescence subsides, and then the mixture is heated at 90° for 0.5 hour. To this mixture cooled to 20° is added dropwise with stirring 9.7 g (63 mmoles) of 3,4-difluoronitrobenzene. A slight exotherm is observed, and the mixture is refluxed (110° ) for 64 hours. Water (300 ml) is added to the cooled mixture, and it is extracted with CH2Cl2 (200 ml). The CH2Cl2 layer is washed with water (3×300 ml), and the four separate wash water portions are extracted in succession with the same 200 ml of CH2Cl2. The combined organic layers are dried, and concentrated to give 31.5 g of solid crude product, which is chromatographed on silica gel (3100 g), eluting with CH2Cl2, and taking 500 ml fractions. Fractions 14 and 15 contain 12.6 g of white solid product, m.p. 110.1 - 118.2, as confirmed by nmr spectroscopy.
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