Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethylene carbonate | HCID 7303 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Bromo-2-ethylphenol | HCID 87877 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 23134202 | HCID 23134202 | 82.1% |
Reaction Steps
To a solution of 2-ethyl-4-bromophenol (3.5 g, 17.4 mmol) and ethylene carbonate (3.22 g, 37 mmol) in NMP (60 mL) was added potassium carbonate (5.17 g, 37.4 mmol). The resulting mixture was heated to 125° C. and maintained for 3 h. The reaction was cooled and poured into water (250 mL) and extracted with EtOAc (2×100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (10–20% EtOAc in hexanes) to give the product (3.5 g, 82% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ: 1.19 (t, J=7.6 Hz, 3 H), 1.89 (brs, 1 H), 2.61 (q, J=7.6 Hz, 2 H), 4.05 (m, 4 H), 6.70 (d, J=8.7 Hz, 1 H), 7.24 (m, 2 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07148226B2 |
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| Source dataset | uspto-grants-2006_12 |
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| ORD ID | ord-a07a621d57934e4fac13c754439aac06 |
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| Source note | uspto-grants-2006_12 |
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