HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → HCID 178466251, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Butylamine | HCID 8007 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | 2,6-Difluoro-3-methoxybenzaldehyde | HCID 599073 | — |
| Reactant | HCID 178418443 | HCID 178418443 | — |
| Catalyst | Manganese(2+) dichloride | HCID 10313134 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178466251 | HCID 178466251 | — |
Reaction Steps
Prepared in analogy to Example 72(a)-(e) from 2,6-difluoro-3-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in toluene, then treatment with 3 equivalents of ethylmagnesium bromide and manganese(II) chloride in tetrahydrofuran and ether followed by chromatography on silical gel, then treatment with boron tribromide in dichloromethane, then treatment with iodoethane and potassium carbonate in N,N-dimethylformamide, then treatment with in situ prepared (1-trityl-1H-imidazol-4-yl)-magnesium halide in dichloromethane, and then treatment with triethylsilane and trifluoroacetic acid in dichloromethane in a pressure tube at 70° C. for 16 h. Amorphous white solid. MS (ISP): 259.3 ([M+H]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158668B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-43eb5dcb246e4b499a808323ac546612 |
| Source note | uspto-grants-2012_04 |