Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | 5-Bromothiophene-3-carboxylic acid | HCID 12039978 | — |
| Solvent | Water | HCID 962 | — |
| Product | 1397285-28-7 | HCID 86706808 | 95% |
Reaction Steps
Under a nitrogen atmosphere, 5-bromo-3-thiophenecarboxylic acid (12 g, 58 mmol) was added to THF (300 ml), and LDA (174 mmol, 232 ml, 0.75 M) was slowly dropped at −78° C. Then, the mixture was stirred for two hours at −30° C., and DMF was slowly dropped at −78° C. Then, water was added to the reaction solution. The reaction solution was then extracted with ethyl acetate, and an organic layer was washed with a saturated saline solution and water. The organic layer was dried with anhydrous magnesium sulfate, and, after filtration, the solvent was distilled off under reduced pressure. With this, a target substance was obtained as a solid (95% yield, crude product). 1H-NMR (400 MHZ, CDCl3, TMS) δ 10.44 (s, 1 H), 7.63 (s, 1 H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09312491B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-7d1fd3878b79454ea0308b6297c86e8f |
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| Source note | uspto-grants-2016_04 |
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