8-Methylquinoline → 5-Bromo-8-methylquinoline

HRID 1189879

반응식

HRID 1189879 반응식
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2.[OH-].[Na+]>OS(O)(=O)=O>[Br:8][C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2

참가 물질

5

반응물 3

HCID 119108-MethylquinolineHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

생성물 1

HCID 47150225-Bromo-8-methylquinoline수율 97.9%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
5 °C

실험 절차

NBS (13.7 g, 76.9 mmol, 1.1 equiv) was added portionwise to a cold (5° C.) solution of 8-methyl-quinoline (10 g, 69.9 mmol) in concentrated H2SO4 (150 mL). The reaction mixture was stirred for 18 h at 5° C., diluted in ice (300 mL) and basified by addition of an aqueous solution of NaOH (10% wt). The resulting white solid was collected by vacuum filtration, rinsed with water, and dissolved in DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to afford 15.2 g of the title compound as a beige solid: ESI-MS: 221.9/223.9 [M+H]+; tR=3.59 min (System 1).

후처리

  1. filtrationThe resulting white solid was collected by vacuum filtration
  2. washrinsed with water
  3. dissolutiondissolved in DCM
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eb16b44c7b2e464a942d23d6c634c094
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674099B2

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