Allyl bromide → 1-(2-(Allyloxy)ethoxy)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzene

HRID 1175319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175319
[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:21])=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[H-].[Na+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[CH2:26]([O:7][CH2:6][CH2:5][O:4][C:3]1[CH:8]=[C:9]([Cl:21])[C:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=2)=[CH:11][C:2]=1[Br:1])[CH:25]=[CH2:24]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 595577142-(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol

Produkt 1

HCID 595577091-(2-(Allyloxy)ethoxy)-2-bromo-5-chloro-4-(4-ethylbenzyl)benzeneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol (AU) (1.85 g, 5 mmol) in anhydrous DMF (10 mL), NaH (0.36 g 15 mmol) was added in portions, and the mixture was stirred at room temperature for 2 hours. Then allyl bromide (1.82 g, 15 mmol) was added dropwise, and the mixture was heated to 45° C. overnight. The reaction was quenched with the saturated NH4Cl and the mixture was extracted with EtOAc, and then washed with water and brine. After drying with anhydrous Na2SO4, the organic portion was filtered and concentrated. The residue was purified by flash chromatography to give AV as an oil (1.74 g, yield 85%). 1H-NMR (CDCl3, 300 MHz) δ 7.31 (s, 1H), 7.13 (m, 4H), 6.94 (s, 1H), 5.94 (m, 1H), 5.26 (m, 2H), 4.14 (m, 4H), 3.96 (s, 2H), 3.84 (m, 2H), 2.64 (q, J=7.5 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H).

Aufarbeitung

  1. temperaturethe mixture was heated to 45° C. overnight
  2. customThe reaction was quenched with the saturated NH4Cl
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialAfter drying with anhydrous Na2SO4
  6. filtrationthe organic portion was filtered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-be2cfe62a028479a99bf001549c84027
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838498B2

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