Ammonium Chloride → 2-Methoxy-1-phenylnaphthalene

HRID 563454

Reaktionsgleichung

Reaktionsgleichung von HRID 563454
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C.C(COC)OC.O>[CH3:13][O:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

10

Edukt 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 728601-Bromo-2-methoxynaphthalene

Produkt 1

HCID 113222662-Methoxy-1-phenylnaphthaleneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

In a flask charged with 1-bromo-2-methoxynaphthalene (20.0 g, 84.4 mmol), phenylboronic acid (11.3 g, 92.8 mmol), palladium acetate (0.10 g, 0.46 mmol), triphenylphosphine (0.85 g, 2.78 mmol) and potassium phosphate (40.9 g, 177.9 mmol), mixture of water (60 mL) and dimethoxyethane (120 mL) was added, and the resultant mixture was heated under reflux for 6 hours. After cooling to ambient temperature, aqueous ammonium chloride (150 mL) and diethyl ether (200 mL) were charged thereto. The organic layer was isolated, and the residue was extracted with diethyl ether. Combined organic layer was dried over magnesium sulfate, and evaporated to remove the volatiles. Purification via silica gel column chromatography (eluent: hexane) gave 2-methoxy-1-phenylnaphthalene (13.0 g, yield: 66%) as colorless liquid.

Aufarbeitung

  1. additionwas added
  2. temperatureunder reflux for 6 hours
  3. customThe organic layer was isolated
  4. extractionthe residue was extracted with diethyl ether
  5. dry with materialCombined organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customto remove the volatiles
  8. customPurification via silica gel column chromatography (eluent: hexane)

Quellen und Nachweise

ORD-Eintrag
ord-478e6e1c71fe4c42a26002ea40ca122f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067511B2

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