Potassium Carbonate → 3,5-Bis(4-cyanophenoxy)benzoic acid ethyl ester

HRID 1024763

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].BrC[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([O:11][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH:8]=[C:7]([O:12][C:22]2[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=2)[CH:6]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 35 °C

Versuchsvorschrift

To a solution of 3,5-dihydroxy benzoic acid ethyl ester 1.2 g (6.58 mmol), dissolved in 10 ml DMF, was added K2CO3 3.63 g (26.32 mmol) followed by 4-bromomethyl-benzonitrile 5.16 g (26.32 mmol) in 5 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and then heated to 35° C. for 8 h. The solvent was removed under reduced pressure and the residue was dissolved in 200 ml of ethyl acetate. The organic layer was washed with brine and water. Organic phase was dried over anhydrous sodium sulphate and solvent was removed under reduced pressure. The crude product was subjected to column chromatography and eluted using hexane:ethyl acetate (8:2) to afford 2.1 g of purified product. 1H NMR (DMSO-d6): 1.3 (3H, t), 4.3 (2H, q), 5.3 (4H, s), 7.0 (1H, s), 7.18 (2H, s), 7.64 (4H, d), 7.86 (4H, d).

Aufarbeitung

customto attain RT
customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in 200 ml of ethyl acetate
washThe organic layer was washed with brine and water
dry with materialOrganic phase was dried over anhydrous sodium sulphate and solvent
customwas removed under reduced pressure
washeluted

Quellen und Nachweise

ORD-Eintrag: ord-b5c6d602a92b44d98da914997540678f
Quelldatensatz: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08722930B2

Verknüpfte Notizen

Wird geladen…