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

HRID 1694681
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HRID 1694681 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-36dcfc905ad84df7a82bcd2c69093e50
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158820B2

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