Diethyl Sulfate → 2-Bromo-7-ethoxynaphthalene

HRID 891957

Reaktionsgleichung

Reaktionsgleichung von HRID 891957
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([OH:12])=[CH:9]2)=[CH:4][CH:3]=1.S(OCC)(O[CH2:17][CH3:18])(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(#N)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][C:8]([O:12][CH2:17][CH3:18])=[CH:7][CH:6]=2)[CH:11]=1

Komponenten

6

Edukt 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 6138277-Bromo-2-naphthol

Produkt 1

HCID 222401492-Bromo-7-ethoxynaphthaleneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 7-bromo-naphth-2-ol (1.0 g, 4.5 mmol, prepared according to patent WO 0146187 A1) in acetonitrile (10 ml) was added diethyl sulfate (1.04 g, 6.7 mmol), K2CO3 (0.92 g) and tetrabutylammonium bromide (10 mg). The reaction mixture was refluxed for 1 hour, poured on water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to provide 2-bromo-7-ethoxynaphthalene (89%), MS: m/e=252 (M+).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. additionpoured on water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-258293cb967e432aaa11dcbe01b4630c
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005432B2

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