Ethyl Acetate → 5-Bromo-3-(trifluoromethyl)quinoline

HRID 2098037ノート

反応式

HRID 2098037 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[Br:15]N1C(=O)CCC1=O.[OH-].[Na+].C(OCC)(=O)C>S(=O)(=O)(O)O.S([O-])([O-])=O.[Na+].[Na+]>[Br:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:14])=[CH:12]2.[Br:15][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=[N:5]2

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 120251663-(Trifluoromethyl)quinoline

生成物 2

HCID 469415118-Bromo-3-(trifluoromethyl)quinolineHCID 687590145-Bromo-3-(trifluoromethyl)quinoline収率 37%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒HCID 24437Sodium Sulfite溶媒

実験手順

3-(Trifluoromethyl)quinoline (7.00 g, 35.5 mmol) and N-bromosuccinimide (9.00 g, 50.6 mmol) in concentrated sulfuric acid (50 ml) was heated to 50° C. After stirring for 1.5 h, the solution was cooled to ambient temperature, diluted with saturated aq. sodium sulfite, made alkaline with 3 N aq. sodium hydroxide, and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 99:1, 49:1, 24:1, and 23:2 hexane:ethyl acetate as the eluant to afford 4.55 g of impure 8-bromo-3-(trifluoromethyl)quinoline and 3.89 g (37% yield) of 5-bromo-3-(trifluoromethyl)quinoline. Method [8] Retention time 6.75 and 7.47 min by HPLC (M+=276 and 278) and (M+=276 and 278).

後処理

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 99:1, 49:1, 24:1, and 23:2 hexane

出典と根拠

ORDレコード
ord-2e7e3e148aca4ae9a54f369622779e32
出典データセット
uspto-grants-2013_05
特許番号
US08450363B2

反応ノート

読み込み中…