HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbon tetrabromide → 6-Bromomethyl-5-cyclopropyl-pyridine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbon tetrabromide | HCID 11205 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 5-Cyclopropyl-6-hydroxymethyl-pyridine-2-carbonitrile | HCID 86674771 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-Bromomethyl-5-cyclopropyl-pyridine-2-carbonitrile | HCID 86674770 | 74% |
Reaction Steps
A solution of 5-cyclopropyl-6-hydroxymethyl-pyridine-2-carbonitrile (0.1 g, 0.6 mmol), CBr4 (0.8 g, 1.2 mmol), PPh3 (0.3 g, 1.2 mmol) in THF (10 mL) was stirred for 12 h at 40° C. The solvent was removed under reduced pressure and the crude product purified by flash column chromatography (silica gel, 3 g, eluting with 25% ethyl acetate in petroleum ether) to give the title compound (0.1 g, 74%) as yellow solid; MS (EI): m/e=236.9 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321727B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-502a375eae9643c9942893df2127a958 |
| Source note | uspto-grants-2016_04 |