反应详情

To a solution of ((4-iodophenyl)ethynyl)trimethylsilane (5) (2.07 g, 6.23 mmol) in methanol (40 mL) was added K2CO3 (8.0 g, 57.9 mmol) and the reaction was allowed to stir for 48 hours. The volatiles were then removed in vacuo and the residue partitioned between ethyl acetate and H2O. The layers were separated and the aqueous phase re-extracted with ethyl acetate (2×). The combined organic layers were washed (H2O, brine), dried (Na2SO4), and filtered. The solvent was removed in vacuo and the residue was crystallized from hexane at −20° C. (in 2 crops) to give 1-ethynyl-4-iodobenzene (6) as a colorless solid (0.92 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ 7.66 (app d, J=8.6 Hz, 2H), 7.20 (app d, J=8.5 Hz, 2H), 1.54 (s, 1H).

1. customThe volatiles were then removed in vacuo
2. customthe residue partitioned between ethyl acetate and H2O
3. customThe layers were separated
4. extractionthe aqueous phase re-extracted with ethyl acetate (2×)
5. washThe combined organic layers were washed (H2O, brine)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. customThe solvent was removed in vacuo
9. customthe residue was crystallized from hexane at −20° C. (in 2 crops)