Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | o-Xylyl bromide | HCID 6992 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Cyanocyclobutane | HCID 78148 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 65376405 | HCID 65376405 | — |
Reaction Steps
n-BuLi (0.018 mol, 7.2 ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at −78° C. After 5 minutes neat cyclobutancarbonitrile (1.2 g, 0.015 mol) was added and the mixture was stirred at −78° C. for 1 hour. Then a solution of 1-(bromomethyl)-2-methylbenzene (3.3 g, 0.018 mol) in THF (3 mL) was added and the mixture was stirred at −78° C. for 1 hour. The mixture was quenched with water and extracted with EtOAc. The organic phase was concentrated and the residue was directly used to the next step without further purification. MS: m/z 186 (M+H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772500B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-355a28d43c764865a3d20737b93a581f |
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| Source note | uspto-grants-2014_07 |
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