Hydrochloric Acid → 3-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid

HRID 1439043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1439043
Br[CH2:2][C:3]([OH:5])=[O:4].[Br-].C([Zn+])C=C.C(Br)C=C.[C:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])=[CH:20][CH:19]=1)(=[O:17])[CH3:16].[Na+].[Br-].Cl>C1COCC1.[Zn].[Hg](I)I>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18]([C:15]([OH:17])([CH3:16])[CH2:2][C:3]([OH:5])=[O:4])=[CH:19][CH:20]=1

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 7841Allyl bromideHCID 1045421-(2',4'-Difluoro(1,1'-biphenyl)-4-yl)ethan-1-oneHCID 253881Sodium BromideHCID 178455868HCID 178455868, Verbindung

Produkt 1

HCID 213225833-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysator3×HCID 24485Mercuric IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel4×

Versuchsvorschrift

A solution of 12.9 g. of bromoacetic acid in 50 ml. of THF is added slowly dropwise at 10°-15° to a solution of 19 g. of allyl-zinc bromide in 200 ml. of THF, prepared by reacting allyl bromide with zinc filings in THF. A solution of 23.2 g. of 4-acetyl-2',4'-difluorobiphenyl in 100 ml. of THF, 6.5 g. of zinc filings, 100 mg. of HgI2 and 10.3 g. of NaBr are added to the reaction mixture, which contains an intermediate of the formula BrCH2 -COOZnBr, and heated under reflux until all the zinc has dissolved. After the alcholate formed has been decomposed with dilute hydrochloric acid, the mixture is worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid, m.p. 121°-123°.

Aufarbeitung

  1. temperatureheated
  2. dissolutionhas dissolved
  3. customAfter the alcholate formed

Quellen und Nachweise

ORD-Eintrag
ord-9e120e94955749679e8839c788553997
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04057647

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