HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-Methylthio-5-nitro anisole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Iodo-2-methoxy-4-nitrobenzene | HCID 230103 | — |
| Reactant | Sodium methanethiolate | HCID 4378561 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Methylthio-5-nitro anisole | HCID 607936 | 68.4% |
Reaction Steps
2-Iodo-5-nitroanisole (5.58 g, 20.0 mmol), Pd2(dba)3 (0.025 eq, 457 mg), Xantphos (0.05 eq, 578 mg), Hunigs Base (1 eq, 3.48 ml) and sodium methanethiolate (1 eq, 1.40 g) were dissolved in THF. The mixture was heated to reflux overnight. Upon cooling the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (4:1 Hexanes/Ethyl Acetate) to give 2-methoxy-1-methylsulfanyl-4-nitro-benzene (2.72 g, 68.3%) as a yellow crystalline solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153809B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-17817b9a6eb54073be343c4ddd317c4a |
| Source note | uspto-grants-2012_04 |