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Cesium fluoride → tert-Butyl {[5-chloro-4'-(ethylthio)biphenyl-2-yl]oxy}acetate

HRID 1694681
ノート
印刷プレビュー

反応式

HRID 1694681 の反応式
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([S:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)[CH3:19].[F-].[Cs+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])=[C:10]([C:24]2[CH:25]=[CH:26][C:21]([S:20][CH2:18][CH3:19])=[CH:22][CH:23]=2)[CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 27343534-Ethylthiophenylboronic acidHCID 49766393tert-Butyl (2-bromo-4-chlorophenoxy)acetate

生成物 1

HCID 86609213tert-Butyl {[5-chloro-4'-(ethylthio)biphenyl-2-yl]oxy}acetate

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of the product from step (i) (2 g), 4-(ethylthio)phenylboronic acid (1.5 g), cesium fluoride (2 g) and Pd(dppf)Cl2 (0.2 g) in dioxane (40 ml) was heated under reflux for 3 h. After cooling the mixture was partitioned between diethylether and water. The organics were separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5% EtOAc/iso-hexane. Yield 0.92 g

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling the mixture
  4. customwas partitioned between diethylether and water
  5. customThe organics were separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica eluting with 5% EtOAc/iso-hexane

出典と根拠

ORDレコード
ord-36dcfc905ad84df7a82bcd2c69093e50
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158820B2

反応ノート

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