8-Methylquinoline → 5-Bromo-8-methylquinoline

HRID 43194

반응식

HRID 43194 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-67903072b86b4e06a90817a7d602ffbc
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536175B2

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