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Ethyl bromoacetate → (4-chloro-2-fluoro-9-trifluoromethyl-9H-fluoren-9-yloxy)-acetic acid ethyl ester

HRID 541116
ノート
印刷プレビュー

反応式

HRID 541116 の反応式
[Cl:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[C:6]=2[CH:5]=[C:4]([F:16])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)[C:25]([F:28])([F:27])[F:26].[F-].[Cs+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>O.CN(C)C=O>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][O:15][C:7]1([C:25]([F:28])([F:27])[F:26])[C:6]2[CH:5]=[C:4]([F:16])[CH:3]=[C:2]([Cl:1])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 594925814-Chloro-2-fluoro-fluoren-9-one

生成物 1

HCID 59492796(4-chloro-2-fluoro-9-trifluoromethyl-9H-fluoren-9-yloxy)-acetic acid ethyl ester

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of dimethylformamide (1000 ml) and 4-chloro-2-fluoro-fluoren-9-one (204 g) was added potassium carbonate (36.4 g), and the mixture was stirred in a water bath. To this mixture was added dropwise trimethyl(trifluoromethyl)silane (156 ml) over 30 min, and the mixture was further stirred at room temperature for 30 min. To the reaction mixture was added cesium fluoride (173 g), ethyl bromoacetate (75 ml) was added dropwise over 20 min, and the mixture was stirred at room temperature. Water (1000 ml) was added to the reaction mixture, and the mixture was placed in a separatory funnel, and extracted with ethyl acetate (1000 ml). The organic layer was washed twice with brine (water:saturated brine=4:1, 1000 ml) and once with saturated brine (500 ml), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (360 g). The obtained residue was directly used for the next reaction without further purification.

後処理

  1. stirringthe mixture was further stirred at room temperature for 30 min
  2. additionwas added dropwise over 20 min
  3. stirringthe mixture was stirred at room temperature
  4. customthe mixture was placed in a separatory funnel
  5. extractionextracted with ethyl acetate (1000 ml)
  6. washThe organic layer was washed twice with brine (water:saturated brine=4:1, 1000 ml) and once with saturated brine (500 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-d6da105f61e44521b28cad89a7e7c612
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871934B2

反応ノート

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