Dimethyl Sulfate → 2-Bromo-1-methoxynaphthalene

HRID 1871625

Reaktionsgleichung

Reaktionsgleichung von HRID 1871625
[C:1]1(O)C2C(=CC=CC=2)C=CC=1.[Br:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[OH:23].BrNC(C)(C)C.C(=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[Br:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[O:23][CH3:1]

Komponenten

7

Edukt 5

HCID 6497Dimethyl SulfateHCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 1508492-Bromo-1-naphthol2×HCID 11789384N-bromo-t-butylamine

Produkt 1

HCID 126128302-Bromo-1-methoxynaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

1-naphthol was converted into 2-bromo-1-naphthol by reaction with a slurry of N-bromo-t-butylamine at -78° C. according to the procedure described in Pearson, Wysong, Breder, J. Org. Chem., 32, 2358 (1967). To a solution of 1 mole (crude) of the bromonaphthol in 750 mL of acetone was added 175 g of potassium carbonate. Over a 2-hour period, 95 mL of dimethylsulfate was added dropwise to the mechanically stirred reaction mixture. The resulting slurry was stirred at 25° C. overnight. The solids were filtered and the solution was stripped to yield a dark brown oil. Initial purification was accomplished by vacuum distillation (80-120° C., 0.2 Torr) followed by further purification by HPLC with hexane to yield 145 g of 2-bromo-1-methoxynaphthalene as a pale yellow oil. NMR confirmed the structure.

Aufarbeitung

  1. filtrationThe solids were filtered
  2. customto yield a dark brown oil
  3. customInitial purification
  4. distillationwas accomplished by vacuum distillation (80-120° C., 0.2 Torr)
  5. customfollowed by further purification by HPLC with hexane

Quellen und Nachweise

ORD-Eintrag
ord-8892f8ab1d414635ac31f0c310d243eb
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103912

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