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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence