HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-(4-Iodophenyl)ethan-1-one | HCID 72869 | — |
| Reactant | HCID 178419189 | HCID 178419189 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one | HCID 2760596 | 64% |
Reaction Steps
4-Iodo acetophenone (10.00 g, 40.64 mmol), PdCl2(dppf).CH2Cl2 (1.00 g, 1.22 mmol) dry dioxane (160 mL) and Et3N (17.0 mL, 121.96 mmol) were combined in a dry flask which had been purged with N2 several times. Pinacol borane (8.80 mL, 60.96 mmol) was added and the reaction mixture was heated at reflux for 4 h then cooled to ambient temperature, poured into Diethyl ether (250 mL) and extracted with H2O and washed with brine. The Diethyl ether was dried (MgSO4), filtered and the filtrate concentrated in vacuo. Purification by gradient chromatography on silica (hexane, 5% EtOAc/hexane) followed by recrystallization (hexane) gave 6.4 g (64%) of the intermediate title compound as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07034045B1 |
| Source dataset | uspto-grants-2006_04 |
| ORD ID | ord-157d29ffa61d4af4ad164d4c83a9bf37 |
| Source note | uspto-grants-2006_04 |