HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-(Ethylsulfanyl)-5-fluorobenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Bromo-5-fluorobenzonitrile | HCID 93654 | — |
| Reactant | Sodium ethanethiolate | HCID 4459711 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-(Ethylsulfanyl)-5-fluorobenzonitrile | HCID 63667696 | 40% |
Reaction Steps
(Step 1) A mixture of 2-bromo-5-fluorobenzonitrile (5.0 g), sodium ethanethiolate (2.31 g), Pd2(dba)3 (114 mg), Xantphos (145 mg) and N,N-diisopropylethylamine (6.46 g) was stirred in toluene (100 ml) at 90° C. for 9 hr under a nitrogen atmosphere. The reaction mixture was treated with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19) to give 2-(ethylsulfanyl)-5-fluorobenzonitrile (1.81 g) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07985863B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-935df9bbcaec4dd0a0447281d1fbb28d |
| Source note | uspto-grants-2011_07 |