tert-Butyl acrylate → 3-(3-Fluoro-4-formyl-phenyl)-acrylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-2-fluoro benzaldehyde (2 g, 9.9 mmol) in DMF (50 ml) and triethylamine (6 ml) was degassed flushing N2 for 30 min. PPh3 (130 mg, 0.459 mmol), Pd(OAc)2 (44.3 mg, 0.20 mmol), NaHCO3 (1.6 g, 18.6 mmol) and tert-butyl acrylate (1.27 g, 9.9 mmol) were added and the resulting mixture was heated to reflux for 4 h. Additional tert-butyl acrylate (633 mg) and Pd(OAc)2 (20 mg) were added and the mixture was stirred at 100° C. for 3 h then the solution was diluted with H2O and extracted with Et2O. The organic layer was dried over Na2SO4 and the solvent was evaporated under vacuo to give the crude product that was purified by silica gel chromatography (petroleum ether/EtOAc 95:5). The collected fractions gave 2 g of 3-(3-fluoro-4-formyl-phenyl)-acrylic acid tert-butyl ester.

Provenance & Evidence