Malonic Acid → (2E)-3-(5-BROMO(2-THIENYL))PROP-2-ENOIC ACID

Participants

Reaction Conditions

Reaction Steps

Malonic acid (44.40 g, 426.7 mmol) was added to a mixture of 5-bromothiophene-2-carbaldehyde (50 g, 261.7 mmol), piperidine (2.84 mL) and pyridine (150 mL). The mixture was refluxed for 1 h at 80° C. and than at 100° C. over night. The volatiles were evaporated and the residue was dissolved in water and acidified with hydrochloric acid (pH 2). The crude product was crystallized in ethanol. Yield: 55.24 g (90.5%). 1H NMR (270 MHz, CH3OH-d4) δ ppm 6.14 (d, J=15.83 Hz, 1H) 7.11-7.16 (m, 2H) 7.68 (d, J=16.36 Hz, 1H); MS 233.1 (M−H)+; Purity (HPLC) 94%.

Provenance & Evidence