Hydrochloric Acid → Methyl (E)-3-(4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylate

HRID 270161

Reaktionsgleichung

Reaktionsgleichung von HRID 270161
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17].Cl.C(OCC)(=O)C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2](/[CH:17]=[CH:16]/[C:15]([O:19][CH3:20])=[O:18])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 8857Ethyl AcetateHCID 950934-Bromo-4'-hydroxybiphenyl

Produkt 1

HCID 9943013Methyl (E)-3-(4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 80271Tri-o-tolylphosphineKatalysator3×HCID 167845palladium(II) acetateKatalysator3×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2 g (8.03 mmol) of 4-(4-bromophenyl)phenol, 1.1 g (12.8 mmol) of methyl acrylate, 18 mg (0.08 mmol) of Palladium acetate, and 94 mg (0.31 mmol) of tri-(o-tolyl)phosphine in 3.7 ml of triethylamine was refluxed for 6 hours. A further 6 mg of Palladium acetate and 30 mg of tri-(o-tolyl)phosphine were added and heated for an hour, then a further 30 mg of Palladium acetate and 94 mg di tri-(o-toluyl)phosphine were added and heated for 3.5 hours. Then the reaction was acidified with 6M HCl, ethyl acetate was added, and stirred for a time to dissolve the precipitate, the phases were separated, the organic phase dried over Na2SO4 and the solvent evaporated. The crude product (934 mg) was purified by taking up in hexane/ethyl ether and filtered off to give 1.7 g of the title product.

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. temperatureheated for an hour
  3. temperatureheated for 3.5 hours
  4. additionwas added
  5. dissolutionto dissolve the precipitate
  6. customthe phases were separated
  7. dry with materialthe organic phase dried over Na2SO4
  8. customthe solvent evaporated
  9. customThe crude product (934 mg) was purified
  10. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-8bcff28ad0e14b338a260eb9926ea3ba
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449495B2

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