1,5-Dibromopentane → 1-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclohexanecarbonitrile

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Utilizing the general procedure outlined for 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile, [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (400 mg, 1.5 mmol) and 1,5-dibromopentane (250 μL, 1.8 mmol) reacted to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclohexanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.22 (d, 1H), 8.06 (d, 1H), 7.68–7.73 (m, 1H), 7.51–7.55 (m, 2H), 7.28–7.35 (m, 2H), 2.49 (d, 2H), 1.73–2.00 (m, 8H). MS (ESI) 337 (M+H)+.

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