HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → (3-Cyclopropoxyphenyl)boronic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reactant | 1-Bromo-3-cyclopropoxybenzene | HCID 57416951 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (3-Cyclopropoxyphenyl)boronic acid | HCID 67394331 | 37.2% |
Reaction Steps
A mixture of 1-bromo-3-cyclopropoxybenzene (1.36 mmol, 0.289 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (2.11 mmol, 0.321 mmol), PdCl2dppf.DCM (0.14 mmol, 0.112 g), KAcO (6.11 mmol, 0.600 g) in a DMSO (3 ml) was heated at 130° C. for 45 minutes, under argon atmosphere in a microwave oven. Ethyl acetate was added and filtered through celite. The organic phase was washed with water and evaporated. The crude mixture was purified by reverse phase using a water/AcN/MeOH system gradient affording 0.090 g (yield 23%) of the expected product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536165B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-94d740c927e444fe9813916260d9a07a |
| Source note | uspto-grants-2013_09 |