Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromoethyl ethyl ether | HCID 61141 | — |
| Reactant | m-Ethynylphenol | HCID 139144 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86653261 | HCID 86653261 | 96% |
Reaction Steps
3-Ethynylphenol (1.707 g, 12.45 mmol, 1.0 eq.) and 1-bromo-2-ethoxyethane (1.1 eq.) were taken up in DMF (20 mL), and Cs2CO3 (2.2 eq.) was added. The mixture was heated to 90° C. for 16 hours, and then cooled to room temperature. The mixture was diluted with water (50 mL) and EtOAc (30 mL), and the layers were separated. The organic layers were washed with water (2×50 mL) and brine (3×50 mL), and dried (MgSO4). The resulting residue was purified by chromatography (10% EtOAc/hexanes) to yield 1-(2-ethoxyethoxy)-3-ethynylbenzene as an oil (2.63 g, 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08338452B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-afa2a4a0e9ba48a892393901b3f90214 |
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| Source note | uspto-grants-2012_12 |
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