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5-Bromo-2-fluoro-benzaldehyde (5.0 g, 24.6 mmol), malonic acid (5.6 g, 53.7 mmol), and piperidine (0.5 mL, 4.9 mmol) were added to pyridine (11.4 mL). The reaction mixture was stirred at 100° C. for 3 hours and then concentrated under reduced pressure. Distilled water was added to the reaction mixture, which was then filtered. The resulting solid was recrystallized from ethanol to give 1.3 g of the titled compound as a white solid. (0164) 1H NMR (400 MHz, CD3OD) 7.89 (d, 1H), 7.74-7.70 (m, 2H), 7.15 (t, 1H), 6.62 (d, 1H)
5-Bromo-2-fluoro-benzaldehyde (5.0 g, 24.6 mmol), malonic acid (5.6 g, 53.7 mmol), and piperidine (0.5 mL, 4.9 mmol) were added to pyridine (11.4 mL). The reaction mixture was stirred at 100 C. for 3 hours and then concentrated under reduced pressure. Distilled water was added to the reaction mixture, which was then filtered. The resulting solid was recrystallized from ethanol to give 1.3 g of the titled compound as a white solid. (0164) 1H NMR (400 MHz, CD3OD) 7.89 (d, 1H), 7.74-7.70 (m, 2H), 7.15 (t, 1H), 6.62 (d, 1H)
3-(5-bromo-2-fluorophenyl)acryloyl chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With thionyl chloride; at 100.0℃; for 2.0h;
3-(5-Bromo-2-fluoro-phenyl)-acrylic acid (1.3 g, 5.0 mmol) prepared in Step 1 was added to thionyl chloride (10.0 mL). The reaction mixture was stirred at 100 C. for 2 hours and then concentrated under reduced pressure. The resulting residue was concentrated under reduced pressure three times, along with using toluene, to give 1.4 g of the titled compound as an unpurified dark brown liquid. (0166) 1H NMR (400 MHz, CDCl3) 7.86 (d, 1H), 7.70 (d, 1H), 7.56 (t, 1H), 7.07 (t, 1H), 6.75 (d, 1H)
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