4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

Temperature

30 °C

A mixture of 4-hydroxybenzaldehyde (10.0 g, 82 mmol) and potassium carbonate (46 g, 326 mmol) was placed into 2 L round bottom flask, and DMF (150 mL) was added. The mixture was stirred for 45 min. and dibromoethane (46 g) was added in one portion, then the reaction mixture was allowed to stir at 25-35° C. for 96 hrs under a nitrogen atmosphere. The reaction mixture was cooled to 25-35° C. and then poured into water (500 mL). The mixture was extracted with EtOAc (3×100 mL), combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography over silicagel by using 10-15% ethyl acetate/pet. ether to afford the title compound (8.50 g, 45%) as a white solid.

1. customwas placed into 2 L round bottom flask
2. stirringto stir at 25-35° C. for 96 hrs under a nitrogen atmosphere
3. extractionThe mixture was extracted with EtOAc (3×100 mL)
4. dry with materialwere dried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by column chromatography over silicagel

ORD record

ord-e2e67af08c8443899325763055b2d956

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456288B2