HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → HCID 15405429, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4-Bromo-1-fluoro-2-methoxybenzene | HCID 13604909 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylamine | HCID 674 | — |
| Product | HCID 15405429 | HCID 15405429 | — |
Reaction Steps
4-Bromo-2-methoxyfluorobenzene (obtainable from 5-bromo-2-fluorophenol by reaction with dimethyl sulfate under basic conditions) is reacted with trimethylsilylacetylene with catalysis by bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide in dimethylamine at 20° C. to give 1-(4-fluoro-3-methoxyphenyl)-2-(trimethylsilyl)ethyne; after filtration chromatography (SiO2/dichloromethane), the crude product is stirred in methanol for 1 hour at 20° C. with addition of 1 N aqueous NaOH solution. Removal of the solvent by distillation and chromatography (SiO2/dichloromethane) gives 4-ethynyl-3-methoxyfluorobenzene.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06482478B1 |
| Source dataset | uspto-grants-2002_11 |
| ORD ID | ord-d29991512cb644178c71ed074e092763 |
| Source note | uspto-grants-2002_11 |