Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 4-(4-fluorophenyl)-2-methylbut-3-yn-2-ol | HCID 5163744 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 20481557 | HCID 20481557 | 33% |
Reaction Steps
To a solution of 25.2 g (0.1 mole) of 1-4-(bromophenoxy)-2-diethylaminoethane and 17.8 g (0.1 mole) of 1-fluoro-4-(3-hydroxy-3-methyl-1-butyn-1-yl)benzene in 250 ml of triethylamine are added, under nitrogen, 11.2 g of pulverised potassium hydroxide, 0.7 g of the palladium complex PdCl2 [P(C6H5)3 ]2 and 0.13 g of copper(I) iodide. The reaction mixture is subsequently stirred for 14 hours at 80° C. The reaction mixture is taken up in 250 ml of ether and the solution is washed twice with 100 ml of water and 100 ml of aqueous K2CO3 solution, treated with activated charcoal and evaporated to dryness. Vacuum distillation of the residue yields 9.5 g (33%) of 1-[4-(4-fluorophenylethynyl)phenoxy]-2-diethylaminoethane with a boiling point of 156°-162° C./0.08 mb.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04412856 |
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| Source dataset | uspto-grants-1983_11 |
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| ORD ID | ord-f86f97f87ec243c29694bfca34829621 |
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| Source note | uspto-grants-1983_11 |
|---|
