Potassium Carbonate → 3-((4-Bromo-3,5-dimethylphenoxy)methyl)-3-methyloxetane

HRID 237435

Reaktionsgleichung

Reaktionsgleichung von HRID 237435
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]1([CH3:23])[CH2:22][O:21][CH2:20]1>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:18][C:19]2([CH3:23])[CH2:22][O:21][CH2:20]2)=[CH:4][C:3]=1[CH3:10]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 144860Oxetane, 3-(bromomethyl)-3-methyl-

Produkt 1

HCID 866971023-((4-Bromo-3,5-dimethylphenoxy)methyl)-3-methyloxetane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-3,5-dimethylphenol (3.0 g) and K2CO3 (5.5 g) in N,N-dimethylformamide (10 mL) is added 3-(bromomethyl)-3-methyloxetane (2.95 g). The mixture is stirred for 12 hours at room temperature and then partitioned between saturated aqueous NaHCO3 solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→70:30) to give the title compound. Yield: 3.5 g; LC (method 4): tR=1.81 min; Mass spectrum (ESI+): m/z=285 [M+H]+.

Aufarbeitung

  1. custompartitioned between saturated aqueous NaHCO3 solution and ethyl acetate
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. dry with materialthe combined organic phases are dried (MgSO4)
  4. customThe solvent is evaporated
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→70:30)

Quellen und Nachweise

ORD-Eintrag
ord-7d867147ffd541b38140cb598cd36b86
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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