Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Trifluoromethanesulfonic acid → 5-Bromo-2-chloro-4-hydroxybenzonitrile
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Trifluoromethanesulfonic acid | HCID 62406 | — |
| 반응물 | N-bromobutanimide | HCID 67184 | — |
| 반응물 | 2-Chloro-4-hydroxybenzonitrile | HCID 592797 | — |
| 반응물 | (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 | — |
| 용매 | Acetonitrile | HCID 6342 | — |
| 생성물 | 5-Bromo-2-chloro-4-hydroxybenzonitrile | HCID 53330452 | 65% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US08541380B2 |
| 출처 데이터셋 | uspto-grants-2013_09 |
| ORD ID | ord-0711056d217843be94d291a1aa661bdd |
| 출처 메모 | uspto-grants-2013_09 |