HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxybromide → 3-(2,4-Dichlorophenyl)-2,5-dimethylpyrazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphorus oxybromide | HCID 24613 | — |
| Reactant | Proton sponge | HCID 88675 | — |
| Reactant | 3-(2,4-Dichlorophenyl)-2,5-dimethylpyrazine 1-oxide | HCID 22147291 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(2,4-Dichlorophenyl)-2,5-dimethylpyrazine | HCID 22147351 | 38% |
| Product | 2-Bromo-5-(2,4-dichlorophenyl)-3,6-dimethylpyrazine | HCID 22147425 | 35% |
Reaction Steps
POBr3 (573 mg) was added to the solution of 3-(2,4-dichlorophenyl)-2,5-dimethylpyrazine 1-oxide (270 mg) and proton sponge (197 mg) in CH2Cl2 at 0° C. The reaction mixture was warmed to r.t. for 10 h. The reaction mixture was washed with 1N HCl, NaHCO3 and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica gel Heptane:EtOAC 100:1) gave the title compound (110 mg, 35%) and 3-(2,4-dichlorophenyl)-2,5-dimethylpyrazine (100 mg, 38%). 1H NMR (CDCl3) δ 2.40, 2.71, 7.28, 7.40, 7.54; MS (ESI+) for C12H9Cl2N2Br1 m/z 333.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07041672B2 |
| Source dataset | uspto-grants-2006_05 |
| ORD ID | ord-d5fafed2d75d4a4994e708e52bcea263 |
| Source note | uspto-grants-2006_05 |