HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 1-Fluoro-3-methoxy-5-((4-methoxybenzyl)sulfanyl)benzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 4-Methoxy-alpha-toluenethiol | HCID 80407 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Bromo-5-fluoroanisole | HCID 10822094 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Product | 1-Fluoro-3-methoxy-5-((4-methoxybenzyl)sulfanyl)benzene | HCID 89767862 | 91.4% |
Reaction Steps
To a mixture of 1-bromo-3-fluoro-5-methoxybenzene (5 g), (4-methoxyphenyl)methanethiol (3.76 g), and toluene (100 mL) were added Pd2(dba)3 (0.447 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.564 g) and DIPEA (8.52 mL). The mixture was stirred at room temperature overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (6.20 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238639B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-913009ee3728439fb3464c42344a6a54 |
| Source note | uspto-grants-2016_01 |