Acetic Acid → HCID 66702093, compound

Participants

Reaction Steps

A solution of ethyl 3-(5-bromothiophen-2-yl)-3-oxopropanoate (2.456 g, 8.86 mmol, from Preparation 1, Step 1), 3-fluorobenzaldehyde (1.034 ml, 9.75 mmol), piperidine (0.088 ml, 0.886 mmol) and acetic acid (0.389 ml, 6.8 mmol) in benzene (50 ml) was heated at 85° C. for 6 h using a Dean-Stark trap to remove the formed water. The reaction solution was concentrated. The crude product was dissolved in a small amount of toluene and charged to 80 g silica gel cartridge which was eluted with a 15 min gradient from 0-5% ethyl acetate in hexane to give ethyl 2-(5-bromothiophene-2-carbonyl)-3-(3-fluorophenyl)acrylate as a viscous yellow oil (3.33 g). HPLC: Rt 3.728 min (Method A); LCMS m/z 407.02, 405.02 (M+23)

Provenance & Evidence