Nitrogen → 4-Methoxy-4'-methylbiphenyl

HRID 1018968

Reaktionsgleichung

Reaktionsgleichung von HRID 1018968
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].N#N.ClCCl>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:13][CH:14]=1

Komponenten

9

Edukt 5

HCID 947NitrogenHCID 6344DichloromethaneHCID 77304-BromoanisoleHCID 10340Sodium CarbonateHCID 79799Tolylboronic acid

Produkt 1

HCID 17047594-Methoxy-4'-methylbiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-methylbenzeneboronic acid (10 g, 73.5 mmol), 4-bromoanisole (25 g, 134 mmol) and 2M aqueous Na2CO3 (75 mL, 150 mmol) in DMF (350 mL) was passed N2 for 15 min. [1,1′Bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (1:1) (200mg, 0.24 mmol) was added and the mixture was heated at 85° C. for 4 h. After cooling to r.t., the mixture was diluted with H2O and extracted with EtOAc. The EtOAc extract was washed with brine (2×), dried (anhydrous MgSO4) and concentrated. The residue was dissolved in small amount of CH2Cl2, filtered through a short pack (˜2.5”) of silica gel in a 600 mL sintered glass funnel and washed the silica with hexanes:EtOAc (4:1). The filtrate was evaporated. The residue was swished with hexanes to give a white flake. The mother liquor was concentrated and swished again with hexanes. After 4 cycles, the combined yield of title product was 10.5 g (72% based on the boronic acid used.).

Aufarbeitung

  1. customfor 15 min.
  2. additionwas added
  3. temperatureAfter cooling to r.t.
  4. extractionextracted with EtOAc
  5. extractionThe EtOAc extract
  6. washwas washed with brine (2×)
  7. dry with materialdried (anhydrous MgSO4)
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in small amount of CH2Cl2
  10. filtrationfiltered through a short pack (˜2.5”) of silica gel in a 600 mL sintered glass funnel
  11. washwashed the silica with hexanes:EtOAc (4:1)
  12. customThe filtrate was evaporated
  13. customto give a white flake
  14. concentrationThe mother liquor was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-270324e2bd524d82993aa4b233b3345f
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06486141B2

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