HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 59640701, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Bromo-5-fluorobenzonitrile | HCID 2783330 | — |
| 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 | Toluene | HCID 1140 | — |
| Product | HCID 59640701 | HCID 59640701 | 74.2% |
Reaction Steps
(Step 1) A mixture of 3-bromo-5-fluorobenzonitrile (10.0 g), sodium methanethiolate (3.85 g), Pd2(dba)3 (229 mg), Xantphos (289 mg) and N,N-diisopropylethylamine (12.9 g) was stirred in toluene (100 ml) at 90° C. for 9 hr. 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 3-fluoro-5-(methylsulfanyl)benzonitrile (6.2 g) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481569B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-4f8338eef1af468aa738e5b728f5b739 |
| Source note | uspto-grants-2013_07 |