HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclohexanethiol → HCID 70873927, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclohexanethiol | HCID 15290 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | methyl 3-bromo-5-chloro-2-methylbenzoate | HCID 70874048 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 70873927 | HCID 70873927 | 88.3% |
Reaction Steps
To a stirred solution of methyl 3-bromo-5-chloro-2-methylbenzoate (1.0 g, 3.79 mmol) in 1,4-dioxane was added N,N-diisopropyl ethylamine (0.98 g, 7.59 mmol). The reaction mixture was purged with argon for 20 min. then Pd(OAc)2 (0.042 g, 0.189 mmol), Xanthphos (0.22 g, 0.38 mmol) and cyclohexylthiol (0.44 g, 3.79 mmol) was added to it sequentially and again purged with argon for 10 min. The reaction mixture was then refluxed for 16 h. On completion, water was added, and the product extracted with ethyl acetate. The organic layer was dried over sodium sulphate and the product was purified by silica gel column to afford the title compound (1.0 g, 83%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376422B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-d1b8019c6f4d4700975b70e9187eb820 |
| Source note | uspto-grants-2016_06 |