8-Methylquinoline → 5-Bromo-8-methylquinoline

HRID 1189879

反応式

HRID 1189879 の反応式
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

参加物

5

反応物 3

HCID 119108-MethylquinolineHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

生成物 1

HCID 47150225-Bromo-8-methylquinoline収率 97.9%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eb16b44c7b2e464a942d23d6c634c094
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

関連ノート

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