Potassium Phosphate, Tribasic → 1,8-Bis(2'-methyl-4'-methoxyphenyl)naphthalene

HRID 1525747

Reaktionsgleichung

Reaktionsgleichung von HRID 1525747
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2I)[CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH3:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[CH3:13])[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 6332861,8-DiiodonaphthaleneHCID 2773486(4-Methoxy-2-methylphenyl)boronic acid

Produkt 1

HCID 708193991,8-Bis(2'-methyl-4'-methoxyphenyl)naphthaleneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1,8-diiodonaphthalene, (1.70 g, 4.5 mmol), 2-methyl-4-methoxyphenylboronic acid, 2, (2.20 g, 13.4 mmol), Pd(PPh3)4 (0.78 g, 0.67 mmol) and K3PO4, (4.30 g, 20.1 mmol) in 50 mL toluene was stirred at 100° C. for 18 hours. The resulting mixture was allowed to come to room temperature, quenched with water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (CH2Cl2:hexanes 2:3) afforded 1.65 g (4.5 mmol, >99%) of off-white crystals containing syn- and anti-isomers of 7 in a ratio of 1:3.

Aufarbeitung

  1. customto come to room temperature
  2. customquenched with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (CH2Cl2:hexanes 2:3)

Quellen und Nachweise

ORD-Eintrag
ord-c2f4bed70b264e1cb64b9e60b8139a70
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085511B2

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