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Trifluoromethanesulfonic acid → 5-Bromo-2-chloro-4-hydroxybenzonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Trifluoromethanesulfonic acid | HCID 62406 | — |
| 反応物 | N-bromobutanimide | HCID 67184 | — |
| 反応物 | 2-Chloro-4-hydroxybenzonitrile | HCID 592797 | — |
| 反応物 | (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 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 5-Bromo-2-chloro-4-hydroxybenzonitrile | HCID 53330452 | 65% |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08541380B2 |
| 出典データセット | uspto-grants-2013_09 |
| ORD ID | ord-0711056d217843be94d291a1aa661bdd |
| 出典メモ | uspto-grants-2013_09 |