Hydrochloric Acid → HCID 9886959, Verbindung

HRID 1835642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835642
Br[C:2]([F:15])=[CH:3][CH:4]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH:5]([CH3:7])[CH3:6].[Br-].[O:17]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][Zn+])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O(C1C=C(C=CC=1)CBr)C1C=CC=CC=1.Cl>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Zn].CCCCCC.C(OCC)(=O)C.CN(C)C=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH:4]([CH:5]([CH3:7])[CH3:6])/[CH:3]=[C:2](\[F:15])/[CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:25]=2)=[CH:9][CH:10]=1

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 74057505HCID 74057505, VerbindungHCID 178419776HCID 178419776, Verbindung2×

Produkt 1

HCID 9886959HCID 9886959, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23994ZincKatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, a mixture of 1-bromo-3-(p-chlorophenyl)-1-fluoro-4-methyl-1-pentene, (E)- and (Z)- (0,9 g, 3,1 mmol), tetrakis(triphenylphosphine)-palladium(0) (0,25 g, 0,22 mmol), and N,N-dimethyl-formamide (20 ml) was treated with 5 ml of a 3-phenoxybenzylzinc bromide solution (prepared from 3-phenoxybenzyl bromide (1,3 g, 5,4 mmol) and Rieke zinc (4 ml of a 1,5 molar solution in tetrahydrofuran), and tetrahydrofuran 2.0 ml). The resultant reaction mixture was stirred at room temperature for one hour, treated with an additional 5 ml of the 3-phenoxybenzylzinc bromide solution, stirred at room temperature, and poured into 2 N hydrochloric acid solution. The resultant aqueous mixture was extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel, and 100:1 and 200:1 hexane/ethyl acetate solutions gave the title product (0,35 g) predominately in the (Z)-configuration.

Aufarbeitung

  1. customThe resultant reaction mixture
  2. stirringstirred at room temperature
  3. extractionThe resultant aqueous mixture was extracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

Quellen und Nachweise

ORD-Eintrag
ord-317f2c04d44d4b2e85115947af17a817
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770788B2

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