Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | HCID 22012209 | HCID 22012209 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 22012246 | HCID 22012246 | 49.8% |
Reaction Steps
Sodium cyanide (12 g) was suspended in dimethyl sulfoxide (180 ml) and heated to 80° C. A solution of 3-(3-chloro-1-propyl)-2,3-dihydro-5-fluoro-benzofuran (42 g) in 40 ml of dimethyl sulfoxide was added dropwise followed by heating to 140° C. for 15 min. After cooling ether and water were added, the ether phase separated, washed with water and dried over magnesium sulfate. Removal of solvent in vacuo left a viscous oil which was applied to a silica gel column giving 4-(2,3-dihydro-5-fluoro-benzofuran-3-yl)butyronitrile as an oil (20 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06031099 |
|---|
| Source dataset | uspto-grants-2000_02 |
|---|
| ORD ID | ord-cfae6351b3974feda3da798a97f68342 |
|---|
| Source note | uspto-grants-2000_02 |
|---|
