4-Bromobenzaldehyde → Z-3-(4-Bromo-phenyl)-acrylic acid methyl ester

Temperature

-78 °C

To a solution of [Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid methyl ester (1.0 eq.) and 18—C-6 (5.0 eq.) in THF (0.05M) at −78° C. was added dropwise KN(TMS)2 (1.0 eq.). The mixture was stirred at −78° C. for 15 min then 4-bromobenzaldehyde (1.0 eq.) was added. The final mixture stirred for 1 h at −78° C., poured in saturated aqueous NH4Cl and extracted with Et2O (3×). The combined organic extracts were washed with, brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc 10 to 25%) afforded a mixture of desired material and the starting aldehyde. Upon treatment in CH2Cl2 of the mixture with Amino-Merrifield resin for 10 min, the aldehyde was removed. Filtration and concentration afforded the title compound as an oil.

1. extractionextracted with Et2O (3×)
2. washThe combined organic extracts were washed with, brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customFlash chromatography (Hex:EtOAc 10 to 25%) afforded
7. additiona mixture of desired material
8. customthe aldehyde was removed
9. filtrationFiltration and concentration

ORD record

ord-50a350153d33454d8ab9eebff7a352a9

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153968B2