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TCI Practical Example: Dehydration Reaction of an Amide by Using Cyanuric Chloride
We are proud to present the synthesis of 4-bromobenzonitrile by the dehydration of 4-bromobenzamide by using cyanuric chloride.
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Used Chemicals
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Procedure
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Cyanuric chloride (183 mg, 1.0 mmol, 0.67 eq.) was added to a solution of 4-bromobenzamide (300 mg, 1.5 mmol) in DMF (3 mL) at 0 °C. The mixture was stirred at room temperature for 3.5 hours and quenched with water (15 mL). The solution was extracted with ethyl acetate (15 mL x 3) and the organic layer was washed with 2 mol/L HCl (15 mL), sat. NaHCO3 aq. (15 mL), and brine (15 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, ethyl acetate:hexane = 1:4) to give 4-bromobenzonitrile as a pale white solid (260 mg, 95% yield).
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Experimenter's Comments
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The reaction mixture was monitored by UPLC.
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Analytical Data
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4-bromobenzonitrile
1H NMR (400 MHz, CDCl3); δ 7.64 (d, 2H, J = 8.4 Hz), 7.53 (d, 2H, J = 8.4 Hz).
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Lead Reference
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- (S)-5-Pyrrolidin-2-yl-1H-Tetrazole
