Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester | HCID 17453 | — |
| Reactant | 5-Bromothiophene-2-carbaldehyde | HCID 78428 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 53396028 | HCID 53396028 | 82% |
Reaction Steps
4.2 g (12.5 mmol, 1.2 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 2.0 g (10.4 mmol, 1.0 eq) of 5-bromothiophene-2-carbaldehyde in 15 mL of toluene. The reaction mixture is stirred for 1 hour at 80° C. The reaction is stopped by adding 20 ml of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (80/20 heptane/ethyl acetate). 2.1 g of methyl 3-(5-bromothiophen-2-yl)acrylate are obtained. Yield=82%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08513297B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-5ada3c1687cf45c595f6eb6d804fd16d |
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| Source note | uspto-grants-2013_08 |
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