3-(Methylthio)-1-propanol → (3-(3-Bromo-2-methylphenoxy)propyl)(methyl)sulfane

HRID 237499

Reaktionsgleichung

Reaktionsgleichung von HRID 237499
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:10][S:11][CH2:12][CH2:13][CH2:14]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:14][CH2:13][CH2:12][S:11][CH3:10]

Komponenten

7

Edukt 4

HCID 104483-(Methylthio)-1-propanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 111714303-Bromo-2-methylphenol

Produkt 1

HCID 86697160(3-(3-Bromo-2-methylphenoxy)propyl)(methyl)sulfane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Bromo-2-methylphenol (0.10 g), 3-(methylthio)propanol (0.055 mL), tri-n-butyl phosphine (0.12 g) and 1,1′-(azodicarbonyl)dipiperidine (0.15 g) are stirred in tetrahydrofurane for 16 hours. Water is added and the mixture extracted with diethyl ether. The organic layer is washed with brine, dried (Na2SO4) and volatiles removed under reduced pressure. The product (80 mg) is obtained after column chromatography (silica gel, n-hexane/ethyl acetate gradient 100:0 to 50:50).

Aufarbeitung

  1. extractionthe mixture extracted with diethyl ether
  2. washThe organic layer is washed with brine
  3. dry with materialdried (Na2SO4)
  4. customvolatiles removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ef70e29ed21546b2a8527d437f2c62ee
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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