反应详情

温度

5 °C

4-Bromo-2-fluoro-1-iodobenzene (57 g) was dissolved in diethylamine (66 ml) under nitrogen atmosphere, and then bis(triphenylphosphine)palladium(II) chloride (0.5 g) and copper(I) iodide (0.5 g) were added thereto, followed by stirring. The flask was cooled to 5° C. or lower, and then 4-pentylphenylacetylene (36 g) was added dropwise thereto. After stirring at room temperature for 5 hours, the reaction solution was poured into a mixture of concentrated hydrochloric acid (40 ml) and ice (30 g). After extraction with chloroform, the resultant was washed twice with water, followed by distilling off chloroform therefrom. The residue was distilled under reduced pressure (b.p. 205° to 210° C./3 mmHg), and then recrystallized from a mixed solvent of acetone and methanol to give 4-bromo-2-fluoro-4'-pentyltolane (27 g).

1. stirringAfter stirring at room temperature for 5 hours
2. extractionAfter extraction with chloroform
3. washthe resultant was washed twice with water
4. distillationby distilling off chloroform
5. distillationThe residue was distilled under reduced pressure (b.p. 205° to 210° C./3 mmHg)
6. customrecrystallized from a mixed solvent of acetone and methanol