Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Bromo-4-(methylsulphonyl)benzene | HCID 77014 | — |
| Reactant | 1,1,4,4-Tetramethyl-6-ethynyl-1,2,3,4-tetrahydronaphthalene | HCID 14726549 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 14852935 | HCID 14852935 | 117.2% |
Reaction Steps
3.2 g (0.015 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetylene, 3 g (0.0128 mol) of 4-methylsulfonylbromobenzene, 12.7 g (0.126 mol) of triethylamine, 12.3 mg (0.047 mmol) of triphenylphosphine, 1.9 mg (0.0027 mmol) of bis(triphenylphosphine)palladium(II) chloride and 6.5 mg (0.034 mmol) of copper(I) iodide in 4 ml of dry dimethylformamide were refluxed under nitrogen. After the reaction was complete, the cooled mixture was poured into water, and the mixture was adjusted to pH 5 with dilute hydrochloric acid and extracted with ether. The organic phase was washed with water, dried over sodium sulfate and evaporated to give 5.5 g of a residue which was recrystallized from methanol to provide 3.5 g of the title compound. Melting point: 153°-155° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05087637 |
|---|
| Source dataset | uspto-grants-1992_02 |
|---|
| ORD ID | ord-5bec40458c6f4d97b2ed3264a33ca933 |
|---|
| Source note | uspto-grants-1992_02 |
|---|
