Methyl Acrylate → Methyl (2E)-3-[2-bromo-4-(hydroxymethyl)phenyl]acrylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (3-bromo-4-iodophenyl)methanol (5.3 g, 17 mmol), methyl acrylate (1.97 mL, 21.8 mmol), tetra-N-butylammonium chloride (4.7 g, 17 mmol), palladium acetate (80 mg, 0.03 mmol) and finely grounded potassium carbonate (5.85 g, 42.3 mmol) in N,N-dimethylformamide (20 mL) was stirred at 50° C. for 20 h. The reaction mixture was cooled to room temperature. Ethyl acetate (200 mL) and brine (50 mL) were added, and the mixture was filtered under suction. The filtrate was collected, and aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (5% to 40% ethyl acetate/hexane) to give oil (3.6 g, 90% purity, 70%). 1H NMR (400 MHz, CDCl3): δ 8.03 (d, J=18.2 Hz, 1H), 7.60 (m, 2H), 7.32 (d, J=8.0 Hz, 1H), 6.39 (d, J=16.0 Hz, 1H), 4.71 (d, J=5.5 Hz, 1H). LCMS found for C11H12BrO3 (M+H)+: m/z=271, 273.

Provenance & Evidence