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Thiophenol → (6-Methoxy-2'-phenylsulfanylmethyl-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 38687
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 38687
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24]Br)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[H-].[Na+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][S:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 67430388(2'-Bromomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 67432230(6-Methoxy-2'-phenylsulfanylmethyl-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-Dioxane
Lösungsmittel

Versuchsvorschrift

To a solution of (2′-bromomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.103 g, 0.24 mmol) and thiophenol (0.03 mL, 0.26 mmol) in 1,4-dioxane (2 mL) was added sodium hydride (60% in mineral oil; 0.013 g, 0.29 mmol), and the reaction was stirred for 30 minutes at room temperature. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was acidified and extracted three times with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionextracted three times with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-be16ad000b6448a4b2ba2df3691ede36
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524748B2

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