[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>CC(C)=O>[N:1]1[N:2]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:3]=[N:4][CH:5]=16.3 g of tetrazole, 8.28 g of potassium carbonate and 0.675 g of potassium iodide are added in succession to a solution of 12 g of 4-bromomethylbenzonitrile in 400 ml of acetone and the mixture is then stirred for 19 hours at 40°-45°. The reaction mixture is cooled, filtered and concentrated. The residue is partitioned between CH2Cl2 and water. The organic phase is washed with brine, dried over sodium sulfate and then concentrated by evaporation. Subsequent chromatography (silica gel) yields first, with toluene/ethyl acetate (2:1), 4-(2-tetrazolyl)methyl-benzonitrile [TLC (hexane/ethyl acetate, 1:2) Rf =0.76); 1H-NMR (CDCl3): δ=5.8 (2H, s), 7.4 and 7.7 (4H, m), 8.5 (1H, s) ppm], and then, with ethyl acetate, 4-(1-tetrazolyl)methyl-benzonitrile [TLC (hexane/ethyl acetate, 1:2), Rf =0.36); 1H-NMR (CDCl3): δ=5.63 (2H, s), 7.4 and 7.7 (4H, m), 8.6 (1H, s) ppm].
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