HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2047918Generated: November 2, 2026
Benzyl mercaptan → 2-(Benzylthio)-5-methoxypyridine
https://huagongshe.com/reaction/2047918
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl mercaptan | HCID 7509 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Bromo-5-methoxypyridine | HCID 11148151 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-(Benzylthio)-5-methoxypyridine | HCID 58349831 | 105.7% |
Reaction Steps
To a solution of 2-bromo-5-methoxypyridine (1.13 g) in toluene (15 mL) were added phenylmethanethiol (820 mg), N,N-diisopropylethylamine (1.71 g), tris(dibenzylideneacetone)dipalladium(0) (220 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (278 mg), and the mixture was stirred under an argon atmosphere at 80° C. for 3 hr. The reaction mixture was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=49:1→19:1) to give the title compound as a yellow oil (yield 1.47 g, quantitative).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592597B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-0950c4950f424abb9eb253486d3aad2e |
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| Source note | uspto-grants-2013_11 |
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