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3-Bromo-4-fluorobenzonitrile 1a (2.0 g, 10 mmol), 2-piperidinemethanol 2a (1.4 g, 12 mmol), and cesium carbonate (3.9 g, 12 mmol) were combined in DMSO (20 mL) and heated to 40 °C for 24 h. These reaction conditions gave a trace amount of the desired N-arylated piperidinemethanol 3a. Significant amount of O-arylated piperidinemethanol 3f was isolated (1.9 g, 64% yield)
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3-Bromo-4-fluorobenzonitrile 1a (2.0 g, 10 mmol), 2-piperidinemethanol 2a (1.4 g, 12 mmol), and cesium carbonate (3.9 g, 12 mmol) were combined in DMSO (20 mL) and heated to 40 °C for 24 h. These reaction conditions gave a trace amount of the desired N-arylated piperidinemethanol 3a. Significant amount of O-arylated piperidinemethanol 3f was isolated (1.9 g, 64% yield).
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