HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 3-Ethynyl-2,4-difluoro-1,5-dimethoxybenzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | [(2,6-Difluoro-3,5-dimethoxyphenyl)ethynyl](trimethyl)silane | HCID 89963360 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Ethynyl-2,4-difluoro-1,5-dimethoxybenzene | HCID 86719171 | 95.3% |
Reaction Steps
To a stirred solution of [(2,6-difluoro-3,5-dimethoxyphenyl)ethynyl](trimethyl)-silane (630 mg, 2.33 mmol) in tetrahydrofuran (2 mL)/methanol (2 mL), cesium fluoride (354 mg, 2.33 mmol) was added at room temperature. After 1 hour, the reaction was quenched with saturated aq. NH4Cl, then extracted with methylene chloride. The combined organic layers were dried over MgSO4, concentrated to give the desired product (440 mg, 95%). 1H NMR (300 MHz, CDCl3): δ 6.62 (t, J=7.8 Hz, 1H), 3.89 (s, 7H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388185B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-7f66a31523cb4a178920a52d0ee68cd3 |
| Source note | uspto-grants-2016_07 |