HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → 4'-(Chloromethyl)-6-fluoro-2'-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-3-yl methyl ether
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | (2'-Fluoro-5'-(methyloxy)-2-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-4-yl)methanol | HCID 57706974 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4'-(Chloromethyl)-6-fluoro-2'-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-3-yl methyl ether | HCID 57707165 | 95% |
Reaction Steps
To a stirred solution of 66.15F (0.035 g, 0.10 mmol) in DCM (2.00 mL) and DMF (0.01 mL) at 0° C. was added thionyl chloride (0.01 g, 0.10 mmol). The reaction was then stirred at room temperature for 2 hours and was then concentrated in vacuo. The resulting product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.15G as a colorless oil (0.035 g, 95% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030354B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-368d4acef3564f029c6cad1df277215f |
| Source note | uspto-grants-2011_10 |