Ammonium Chloride → [4-(3,3-Bis-biphenyl-4-yl-allylsulfanyl)-2-methyl-phenoxy]-acetic Acid

HRID 9340

Reaktionsgleichung

Reaktionsgleichung von HRID 9340
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)=[CH:9][CH2:10][S:11][C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=2)=[CH:4][CH:3]=1.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[F-].[K+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1COCC1>[C:2]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)=[CH:9][CH2:10][S:11][C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 10370262{4-[3,3-Bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid

Produkt 1

HCID 9850329[4-(3,3-Bis-biphenyl-4-yl-allylsulfanyl)-2-methyl-phenoxy]-acetic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 178418851HCID 178418851, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (297 mg, 0.54 mmol), phenylboronic acid (152 mg, 1.2 mmol), KF (104 mg, 1.79 mmol), Pd2(dba)3 (30 mg, 33 mmol) and Pd(P(t-Bu)3)2 (33 mg, 65 mmol). THF (6 ml) was added to the solid mixture keeping the mixture under nitrogen. The reaction mixture was stirred at room temperature for 1 h, followed by 4 h at 50° C. A saturated solution of ammonium chloride (5 ml) was added, and the mixture was extracted with dichloromethane (2×20 ml). The organic phases were dried and evaporated. The residue was purified by column chromatography (eluent: dichloromethane:THF (8:3)) to give the title compound in 155 mg (53%) yield.

Aufarbeitung

  1. customIn an evaporated schlenk flask kept under nitrogen atmosphere
  2. waitfollowed by 4 h at 50° C
  3. extractionthe mixture was extracted with dichloromethane (2×20 ml)
  4. customThe organic phases were dried
  5. customevaporated
  6. customThe residue was purified by column chromatography (eluent: dichloromethane:THF (8:3))

Quellen und Nachweise

ORD-Eintrag
ord-98105445b39e4979b24da4a8f78d2882
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091245B2

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