HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl mercaptan → 1-Benzylsulfanyl-3-bromo-5-fluoro-2-methoxy-benzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl mercaptan | HCID 7509 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 1,3-Dibromo-5-fluoro-2-methoxybenzene | HCID 2773965 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 1-Benzylsulfanyl-3-bromo-5-fluoro-2-methoxy-benzene | HCID 66911104 | — |
Reaction Steps
1,3-Dibromo-5-fluoro-2-methoxy-benzene (14.2 g, 50 mmol), phenyl-methanethiol (5.86 ml, 50 mmol), Pd2dba3 (1.145 g, 1.25 mmol, 2.5 mol-%), Xantphos (1.447 g, 2.5 mmol, 5 mol-%) and DIPEA (17.5 ml, 100 mmol) were dissolved in 130 ml dry, degassed 1,4-dioxane and heated to reflux for 3 h. After cooling down the mixture was filtrated and evaporated. The remaining solid (22 g) is chromatographed on silica gel using n-heptane-MTBE as eluent. Yield: 12.42 g, 76%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08378092B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-2644cbe5818049a7b54ec3ec3f50d5bf |
| Source note | uspto-grants-2013_02 |