Water → 2-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde

Temperatur

140 °C

To a stirred suspension of potassium fluoride (1.89 gm, 0.0326 mol) in dry DMSO (10 ml) was added a solution of 2-bromoisovanillin (5.0 gm, 0.0217 mol) in DMSO (10 ml). A solution of 4-fluoronitrobenzene (5.0 gm, 0.0260 mol) in DMSO (5 ml) was added to the above suspension and the reaction mixture was stirred at 140° C. for 4 h. The reaction mixture was cooled to room temperature and the contents were poured into water (150 ml) and extracted with ethyl acetate (50 ml×3). The organic extracts were combined and washed with 1N sodium hydroxide (25 ml×2), water and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated in vacuo and the residue was purified by silica-gel column chromatography using 20% ethyl acetate-petroleum ether as the eluent to give 2-bromo-3-(p-nitrophenoxy)-4-methoxy benzaldehyde as a pale yellow solid (5.0 gm) mp: 132-140° C.

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionextracted with ethyl acetate (50 ml×3)
3. washwashed with 1N sodium hydroxide (25 ml×2), water and brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationThe dried organic layer was concentrated in vacuo
6. customthe residue was purified by silica-gel column chromatography

ORD-Eintrag

ord-7a935dba3ce549eea48a1b6f1eb78cf0

Quelldatensatz

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07384962B2