4-Bromoanisole → HCID 11381397, Verbindung

HRID 1950604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1950604
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+]>O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9](=[O:15])[CH:8]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH2:7][CH2:6]2

Komponenten

6

Edukt 3

HCID 77304-BromoanisoleHCID 114470756,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-oneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 11381397HCID 11381397, VerbindungAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 634876Binap, (A+-)-KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

The title compound was synthesized by referring to J. Am. Chem. Soc., 1997, 119 (45), 11108. To a solution of 6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one (11.9 g) in tetrahydrofuran (200 ml) were sequentially added 4-bromoanisole (16.2 g), sodium tert-butoxide (11.1 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.3 g) and tris(dibenzylidene)acetone dipalladium(0) (792 mg), and the solution was stirred for 1.5 hours at 75° C. under a nitrogen atmosphere. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo; the resulting crude crystal was suspended in diethyl ether and then filtered. The mother liquor was concentrated in vacuo, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate system); the resulting crystal was suspended in diethyl ether, then filtered, and combined to provide the title compound (14.2 g).

Aufarbeitung

  1. customThe title compound was synthesized
  2. extractionThe solution was extracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. filtrationfiltered
  7. concentrationThe mother liquor was concentrated in vacuo
  8. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate system)
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-2bc212f8fbfa43b8b2944f855c37f0d3
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399520B2

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