Potassium Carbonate → 2,6-Bis(3-pyridyl)phenyl benzyl ether

HRID 2069874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069874
[CH2:1]([O:8][C:9]1[C:14](Br)=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>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.CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 145344892-(Benzyloxy)-1,3-dibromobenzene

Produkt 1

HCID 581502802,6-Bis(3-pyridyl)phenyl benzyl etherAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

2,6-Dibromophenyl benzyl ether (25.61 g, 74.88 mmol), 3-pyridylboronicacid (20.25 g, 164.7 mmol), aqueous potassium carbonate (233 mL 2 M), and DMF (370 mL) were put together in a 1 liter flask. Oxygen was removed by several vacuum-argon cycles. Then Pd(PPh3)4 (5.38 g, 4.65 mmol) was added and the mixture was heated to 85° C. under an argon atmosphere. After 48 hr, the reaction mixture was cooled to rt, and poured into an ice/water mixture (1 L). This was extracted with diisopropylether (3 times 300 mL), and the combined organic layers were dried over MgSO4, filtered, and the solvent was removed in vacuo, yielding a yellow crystalline solid. Recrystallisation from diethyl ether yielded the product as a white crystalline solid (10.34 g, 41%). The residue was further purified by column chromatography (silicagel, EtOAc/n-pentane=3:2), yielding another 2.60 g (10%) of the product (total yield 51%). 1H-NMR(CDCl3):δ=8.80 (s, 2H), 8.59 (d, 2H), 7.93 (dd, 2H), 7.65 (d, 2H), 7.34 (m, 3H), 7.19 (t, 1H), 7.10 (t, 2H), 6.64 (d, 2H), 4.15 (s, 2H) ppm.

Aufarbeitung

  1. customOxygen was removed by several vacuum-argon cycles
  2. temperaturethe reaction mixture was cooled to rt
  3. extractionThis was extracted with diisopropylether (3 times 300 mL)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customyielding a yellow crystalline solid
  8. customRecrystallisation from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3aabeaefb4ad412cbc04944299d36e5e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299202B2

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