Trifluoromethanesulfonic acid → 5-Bromo-2-chloro-4-hydroxybenzonitrile

HRID 46227

반응식

HRID 46227 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].ClC1C(CC2SC(C3OC=CC=3)=NN=2)=CC([C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)=C(OC)C=1.OS(C(F)(F)F)(=O)=O.C1C(=O)N([Br:57])C(=O)C1>C(#N)C>[Br:57][C:7]1[C:8]([OH:10])=[CH:9][C:2]([Cl:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

참가 물질

6

반응물 4

HCID 62406Trifluoromethanesulfonic acidHCID 67184N-bromobutanimideHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 49846233(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

생성물 1

HCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile수율 65%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  1. customto quenching with saturated sodium bisulfite
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography (5-40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-0711056d217843be94d291a1aa661bdd
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541380B2

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