HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethyl Ether → 4-((Trimethylsilyl)ethynyl)benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4-Bromobenzenesulfonamide | HCID 69696 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 4-((Trimethylsilyl)ethynyl)benzenesulfonamide | HCID 69517439 | 61% |
Reaction Steps
To a solution of 4-bromobenzenesulfonamide (4.51 g, 19.1 mmole) in toluene (900 mL) at 75° C. was added ethynyl(trimethyl)silane (4 g, 40 mmole), Pd(PPh3)4 (1.3 g, 1.1 mmole), CuI (0.46 g, 2.42 mmole) and TEA (5.7 g, 56 mmole) and the mixture was allowed to cool to room temperature while stirring. Additional Pd(PPh3)4 (1 g, 0.9 mmole) was added and the mixture was stirred at room temperature. After 5 days, ethyl ether was added and the mixture was washed with 10% HCl, H2O, sat. aqueous NH4Cl, dried over Na2SO4 and concentrated in vacuo to give 2.93 g (61% yield) of the product: ESHRMS m/z 271.0935 (M+NH4, C11H15NO2SSiNH4, Calc'd 271.0937).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07259266B2 |
| Source dataset | uspto-grants-2007_08 |
| ORD ID | ord-0e038fba1a464a9d973e1f77b50c97f5 |
| Source note | uspto-grants-2007_08 |