HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Bromoanisole → 1-Ethynyl-4-methoxybenzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Bromoanisole | HCID 7730 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-Ethynyl-4-methoxybenzene | HCID 251020 | — |
Reaction Steps
Using Method D above, 4-bromoanisole (Aldrich) was coupled with trimethylsilylacetylene (Aldrich) using (Ph3P)2PdCl2 and CuI as catalyst in DMF and Et3N as solvent and was heated at reflux for 1 day. The resulting trimethylsilyl derivative was hydrolized with aqueous potassium hydroxide to give 4-methoxyphenyl acetylene.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06313310B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-a517a2329fe34fdead8c15b65bc6b3c3 |
| Source note | uspto-grants-2001_11 |