Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | 2-(3-Bromo-5-methyl-2-benzofuranyl)benzoic acid | HCID 10065258 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 10430277 | HCID 10430277 | 25.7% |
Reaction Steps
A mixture of 2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid (described in EP-A-0434249) (2.0 g), p-toluenesulphonyl chloride (2.5 g), tert-butanol (10 ml) and pyridine (3 ml) was stirred at 0° C. and allowed to warm to room temperature. Stirring was continued for 72 hours. The mixture was then diluted with ether (100 ml) and washed with 2M hydrochloric acid (75 ml) followed by an aqueous solution of 1M sodium bicarbonate (75 ml). The aqueous solutions were further extracted with ethyl acetate (100 ml) and the combined organic extracts were dried and evaporated in vacuo. Purification by flash column chromatography eluting with dichloromethane:hexane (3:7) gave the title compound (0.6 g) as a colourless gum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05317023 |
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| Source dataset | uspto-grants-1994_05 |
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| ORD ID | ord-06af9d81acd0477691eee3120c2adbe3 |
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| Source note | uspto-grants-1994_05 |
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