Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanethiol | HCID 6343 | — |
| Reactant | Diisopropylcarbodiimide | HCID 12734 | — |
| Reactant | Benzoic acid, 2-(diphenylphosphino)- | HCID 87021 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59327676 | HCID 59327676 | 75% |
Reaction Steps
2-(Diphenylphosphanyl)benzoic acid (0.50 g, 1.63 mmol) and DMAP (20 mg, 0.163 mmol) were dissolved in CH2Cl2 (10 mL). Ethanethiol (EtSH, 0.35 mL, 4.89 mmol) was added, and the solution was placed under Ar(g) and cooled to 0° C. DIC (0.25 mL, 1.63 mmol) was added dropwise, and the resulting solution was allowed to warm to room temperature and stirred overnight. The solution was then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography, eluting with 10% EtOAc/hexanes, to give phosphine 1b as a pale yellow solid (0.43 g, 1.22 mmol, 75% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08871916B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-dd3bc0483de74738b5ae1c526048687e |
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| Source note | uspto-grants-2014_10 |
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