Water → 3-(Trifluoromethyl)quinoline

HRID 2098036ノート

反応式

HRID 2098036 の反応式
I[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F-:12].[K+].Cl[C:15]([F:21])([F:20])C(OC)=O.O>CN(C)C=O.C(OCC)(=O)C>[F:20][C:15]([F:21])([F:12])[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

7

反応物 4

HCID 962WaterHCID 73935Methyl chlorodifluoroacetateHCID 522689Potassium FluorideHCID 112538363-Iodoquinoline

生成物 1

HCID 120251663-(Trifluoromethyl)quinoline収率 37%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Iodoquinoline (13.65 g, 53.5 mmol), cuprous iodide (21.12, 111 mmol), potassium fluoride (7.11 g, 122 mmol), and methyl 2-chloro-2,2-difluoroacetate (23 ml, 216 mmol) in dimethylforamide (200 ml) was placed into a preheated oil bath at 120° C. After stirring for 6 h, the solution was diluted water and extracted with diethyl ether. 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, 23:2, 9:1, and 4:1 hexane:ethyl acetate as the eluant to afford 3.89 g (37% yield) of 3-(trifluoromethyl)quinoline. Method [7] retention time 4.67 min by HPLC (M+198).

後処理

  1. extractionextracted with diethyl ether
  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, 23:2, 9:1, and 4:1 hexane

出典と根拠

ORDレコード
ord-6e252b27cd3741be9e42c32dab721bad
出典データセット
uspto-grants-2013_05
特許番号
US08450363B2

反応ノート

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