1,3-Dibromopropane → 1,2-Bis(4-(3-bromopropoxy)phenyl)ethane-1,2-dione

HRID 1620358

Reaktionsgleichung

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][CH2:28][Br:29]>CN(C)C=O>[Br:29][CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:26][CH2:27][CH2:28][Br:29])=[CH:13][CH:12]=2)=[O:10])=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

1,2-bis(4-hydroxyphenyl)ethane-1,2-dione (2.6 g, 10.74 mmol) was dissolved in DMF and K2CO3 (5.9 g, 42.7 mmol) was added, 100 mmol of 1,3-dibromopropane and a catalytic amount of KI were then added. The mixture was heated to 80° C. and stirred for 3 days. TLC check showed 1,2-bis(4-hydroxyphenyl)ethane-1,2-dione disappeared. Dimethylformamide (DMF) was removed, and water was added, extracted by EtOAc, washed with brine, dried over MgSO4. The solvent was removed and the residue was purified by column chromatography to give 1,2-bis(4-(3-bromopropoxy)phenyl)ethane-1,2-dione 6 as a pale yellow solid, as confirmed by the following nuclear magnetic resonance (NMR) data obtained therefrom: 1H NMR (500 MHz, CDCl3): δ 7.94 (d, J=8.8 MHz, 4H), 6.99 (d, J=8.8 MHz, 4H), 4.20 (t, J=6.2 MHz, 4H), 3.61 (t, J=6.2 MHz, 4H), 2.34 (m, 4H) ppm.

Aufarbeitung

customDimethylformamide (DMF) was removed
additionwater was added
extractionextracted by EtOAc
washwashed with brine
dry with materialdried over MgSO4
customThe solvent was removed
customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-a631abe5a25c43389fdf3ed5a2ed2be3
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08772443B2

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