Sodium Iodide → HCID 12615599, compound

Temperature

-78 °C

To a solution of THF (200 mL) into reaction flask was added (5-chloropent-1-ynyl)benzene Phenylacetylene (10 g, 97.91 mmol). Then the reaction mixture was cooled to −78° C. in a dry ice bath. nBuLi (95.95 mmol, 38.39 mL) was added dropwise and allowed to react for 0.5 h at −78° C. At −78° C., 1-bromo-3-chloropropane was added. Stirred for 5 hours during which the reaction was allowed to warm up to room temperature. Then reaction was refluxed at 90° C. for 3 hours. The solvent was distilled off, then water (150 mL) and ether (150 mL) was added. The crude product was extracted, ether was distilled off and the resulting crude mixture was dissolved in acetone. Sodium iodide (22.92 mmol, 3.44 g) was added into the solution. The reaction mixture, with reflux condenser attached, was heated to 70° C. for two days. Acetone was distilled off using short path distillation apparatus. Ether (150 mL) and water (150 mL) was added and carried out extraction. Ether was then dried over magnesium sulfate and distilled off resulting in 5.00 g of product (yield 98%). No further purification was carried out. 1H NMR (500 MHz, CDCl3) □2.072 (m, 2H, CH2); 2.605 (t, 2H, CH2); 3.697 (m, 2H, CH2); 7.276 (m, 2H, Phenyl); 7.389 (m, 2H, phenyl); 7.484 (m, 1H, phenyl).

1. customto react for 0.5 h at −78° C
2. temperatureto warm up to room temperature
3. customThen reaction
4. temperaturewas refluxed at 90° C. for 3 hours
5. distillationThe solvent was distilled off
6. additionwater (150 mL) and ether (150 mL) was added
7. extractionThe crude product was extracted
8. distillationether was distilled off
9. dissolutionthe resulting crude mixture was dissolved in acetone
10. temperatureThe reaction mixture, with reflux condenser
11. temperaturewas heated to 70° C. for two days
12. distillationAcetone was distilled off
13. distillationpath distillation apparatus
14. additionEther (150 mL) and water (150 mL) was added
15. extractioncarried out extraction
16. dry with materialEther was then dried over magnesium sulfate
17. distillationdistilled off

ORD record

ord-8f12ca17a7c7487bb38c3e979beb844c

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987414B2