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

HRID 576319

반응식

HRID 576319 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(S(O)(=O)=O)(F)(F)F.C1C(=O)N([Br:26])C(=O)C1>CC#N>[Br:26][C:7]1[C:8]([OH:10])=[CH:9][C:2]([Cl:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

참가 물질

5

반응물 3

HCID 62406Trifluoromethanesulfonic acidHCID 67184N-bromobutanimideHCID 5927972-Chloro-4-hydroxybenzonitrile

생성물 1

HCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile수율 69.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-chloro-4-hydroxybenzonitrile (10 g, 65.1 mmol) in CH3CN (200 mL) was added CF3SO3H (6.33 g, 71.6 mmol) and NBS (16.2 g, 94.1 mmol) at −30° C. After being stirred for 18 hours at room temperature, the mixture was quenched with aq. saturated NaHSO4 solution and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 37 (10.5 g, 66%) as a white solid.

후처리

  1. customthe mixture was quenched with aq. saturated NaHSO4 solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f9f150884fbd4cf7a5c01ec1c780055b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034921B2

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