Hydrochloric Acid → Methyl (4'-hydroxybiphenyl-3-yl)acetate

HRID 2076592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076592
C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)O1.Br[C:24]1[CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=1.Cl>CN(C)C(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C:28]2[CH:29]=[CH:24][CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=2)=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 11746402Methyl 2-(3-bromophenyl)acetate

Produkt 1

HCID 59219036Methyl (4'-hydroxybiphenyl-3-yl)acetateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21534740N,N-Dimethylacetamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (0) (1.00 g, 0.88 mmol) and potassium carbonate (4.80 g, 37.0 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.84 g, 17.5 mmol) and methyl (3-bromophenyl)acetate (4.00 g, 17.5 mmol) which was synthesized according to the method described in literature (Muller, R. N. et al., Eur. J. Org. Chem., 2002, vol. 23, pp. 3966-3973) in a mixture of N,N-dimethylacetamide-water (10:1, 66 ml), and the mixture was stirred at 110° C. for 6 hours. After the reaction mixture was poured into 0.2N hydrochloric acid and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1) to give methyl (4′-hydroxy-1,1′-biphenyl-3-yl)acetate (2.83 g, yield: 67%).

Aufarbeitung

  1. customwas synthesized
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-1ea0b1dd82e641009b468057c51ae513
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923573B2

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