Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Bromo-4-methylphenol | HCID 10307913 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 89649579 | HCID 89649579 | 54.3% |
Reaction Steps
To a stirred solution of 3-bromo-4-methyl-phenol (1.2 g, 6.42 mmol) in anhydrous DMF (12 mL), was added iodoethane (1.55 mL, 19.25 mmol) and potassium carbonate (1.06 g, 7.7 mmol). The resulting mixture was left to stir at 80° C. for 18 h. It was allowed to cool to room temperature, poured into brine and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and filtered. The filtrate was evaporated and the crude residue was purified by silica gel chromatography (25 g SiO2) eluting with iso-hexane. Evaporation of desired fractions gave 2-bromo-4-ethoxy-1-methyl-benzene (D64) (0.7500 g, 3.4869 mmol, 54.3% yield) as colourless oil;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376436B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-e943bc4469a24c64804a616d93d3d773 |
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| Source note | uspto-grants-2016_06 |
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