HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chlorine → 2-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chlorine | HCID 24526 | — |
| Reactant | 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-methoxy-1H-indole | HCID 10712280 | — |
| Solvent | Boron tribromide | HCID 25134 | — |
| Product | 2-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole | HCID 10616205 | 69.3% |
Reaction Steps
By the method used in Example 1, Part D, 911 mg (2.6 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-methoxy-1H-indole was O-demethylated by treating it with 10 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 590 mg (69% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-hydroxy-1H-indole as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05733923 |
| Source dataset | uspto-grants-1998_03 |
| ORD ID | ord-1b52bb60c1944a8bb041ea0a07e47ab6 |
| Source note | uspto-grants-1998_03 |