HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoromethanesulfonic acid → 5-Bromo-2-chloro-4-hydroxybenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoromethanesulfonic acid | HCID 62406 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 2-Chloro-4-hydroxybenzonitrile | HCID 592797 | — |
| Reactant | (2S,3R,4R,5S,6R)-2-(4-Chloro-5-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-2-methoxyphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol | HCID 49846233 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 5-Bromo-2-chloro-4-hydroxybenzonitrile | HCID 53330452 | 65% |
Reaction Steps
To a solution of 2-chloro-4-hydroxybenzonitrile (compound 86, 10.0 g, 65.1 mmol) in acetonitrile (200 mL) was added triflic acid (10.0 mL, 71.6 mmol) and NBS (16.2 g, 91.2 mmol) at −30° C. The solution was allowed to warm up to room temperature and stirred overnight prior to quenching with saturated sodium bisulfite. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (5-40% EtOAc/hexanes) to yield title compound (9.80 g, 65%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08541380B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-0711056d217843be94d291a1aa661bdd |
| Source note | uspto-grants-2013_09 |