HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 3-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1,3-Benzenediol, 5-chloro- | HCID 94554 | — |
| Reactant | 4-(2-Hydroxyethyl)benzonitrile | HCID 2800815 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenol | HCID 22033534 | 21.3% |
Reaction Steps
Triphenylphoshine (32 g; 122 mmol) and diethylazodicarboxylate (19.2 mL; 122 mmol) were dissolved in CH2Cl2 (150 mL). Chloro-3,5-dihydroxybenzene (9.1 g; 63 mmol; from step (i) above) and 2-(4-cyanophenyl)ethanol (9.04 g; 61 mmol) were added and the solution was stirred at room temperature overnight. The mixture was diluted with Et2O and filtered through Celite. The solvent was removed in vacuo. Purification, first by flash chromatography (SiO2; CH2Cl2:MeOH), then by preparative HPLC (60% CH3CN:0.1 M NH4OAc/aq), afforded 3.55 g (21%) of the sub-title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07074820B2 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-62d2192aded34cdfa64452a6022fb411 |
| Source note | uspto-grants-2006_07 |