8-Methylquinoline → 5-Bromo-8-methylquinoline

HRID 2280999

反応式

HRID 2280999 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12]Br>S([O-])([O-])(=O)=O.[Ag+2].OS(O)(=O)=O>[Br:12][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

参加物

5

反応物 2

HCID 119108-MethylquinolineHCID 24408Bromine2 回

生成物 1

HCID 47150225-Bromo-8-methylquinoline収率 92.4%

試薬・触媒・溶媒 2

HCID 178418844HCID 178418844、化合物触媒HCID 1118Sulfuric Acid溶媒

実験手順

To a solution of 8-Metyl quinoline (30 g, 0.209 mol) in Conc.H2SO4 (300 ml) was added Silver sulphate (97.98 g, 0.314 mol) in lots at 0° C. and followed by Bromine (10.74 ml, 0.209 mol) drop wise for 10 min. After addition of Bromine, the reaction mixture was stirred at RT for 4 h and the reaction completion was confirmed by TLC. After completion of reaction the reaction mixture was quenched with ice and basified with NH4OH solution and extracted with ethyl acetate. The organic layer was washed with water, brine solution and dried over anhydrous sodium sulphate and concentrated to afford (43 g, 92.4% yield) as dark brown liquid. The crude product was as such taken for next step without further purification. 1H NMR (DMSO-d6 400 MHz): δ 8.97-8.96 (dd, J=4.16, 5.8 Hz, 1H), 8.45-8.42 (dd, J=8.56, 10.2 Hz, 1H), 7.81-7.79 (d, J=7.68 Hz, 1H), 7.67-7.64 (dd, J˜8.52, 12.64 Hz, 1H), 7.53-7.51 (dd, J=7.64, 8.52 Hz, 1H), 2.66 (s, 3H).

後処理

  1. customAfter completion of reaction the reaction mixture
  2. customwas quenched with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customto afford (43 g, 92.4% yield) as dark brown liquid
  8. customas such taken for next step without further purification

出典と根拠

ORDレコード
ord-66a43ba4336e4b5e942e34be8bdf21bf
出典データセット
uspto-grants-2015_09
特許番号
US09139568B2

関連ノート

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