HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1930814Generated: November 2, 2026
Ethanethiol → 5-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester
https://huagongshe.com/reaction/1930814
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanethiol | HCID 6343 | — |
| Reactant | N-Boc-5-bromoisoindoline | HCID 16102683 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Bis(cyclopenta-2,4-dien-1-yl-di(propan-2-yl)phosphane);iron(2+) | HCID 15420033 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Solvent | Tetrahydrofuran ethyl acetate | HCID 21939870 | — |
| Product | 5-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester | HCID 57753600 | — |
Reaction Steps
Lit. Tetrahedron 2004, 60, 7397-7403. To a stirred suspension of 1.34 mmol 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (CAS: 201940-08-1) in 2 ml dioxane were added 0.03 mmol 1,1′-bis(diisopropylphosphino)ferrocene, 0.03 mmol palladium acetate, 1.61 mmol sodium tert-butoxide and 2.68 mmol ethanethiol and the mixture was stirred at 100° C. for 16 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate/tetrahydrofuran and washed with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to yield the title compound as a brown oil which was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08188139B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-8ce8b68a559d4ea68f089b0496c5fbda |
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| Source note | uspto-grants-2012_05 |
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