4-Bromophenol → 1-Bromo-4-[3-(methylsulfanyl)propoxy]benzene

HRID 1877194

Reaktionsgleichung

Reaktionsgleichung von HRID 1877194
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][S:10][CH2:11][CH2:12][CH2:13]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:12][CH2:11][S:10][CH3:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 78084-BromophenolHCID 104483-(Methylthio)-1-propanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidine

Produkt 1

HCID 685115371-Bromo-4-[3-(methylsulfanyl)propoxy]benzeneAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-bromophenol (3.4 g) and 3-methylthio-1-propanol (2.6 g) in tetrahydrofuran (20 mL) were added tributylphosphine (7.5 mL) and 1,1′-(azodicarbonyl)dipiperidine (7.6 g), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (0% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give the title compound (4.6 g, 83%) as a white crystal.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column (0% ethyl acetate/hexane to 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-708dcdf0154147748cbbed7f3495007c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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