Benzyl Bromide → Ethyl 3-[3-(benzyloxy)-4,5-difluorophenyl]propanoate

Participants

Reaction Steps

A solution of DMF (21 mL), ethyl 3-(3,4-difluoro-5-hydroxyphenyl)propanoate (2.46 g, 0.0107 mol), and K2CO3 (1.92 g, 0.0139 mol) were combined at 0° C. under N2. After 10 min, benzyl bromide (1.65 mL, 0.0139 mol) was added dropwise. The solution was allowed to warm to room temperature. After 16 h, H2O (50 mL), Et2NH (2 eq) and EtOAc (50 mL) were added and the organic layer isolated. The aqueous layer was washed with EtOAc (2×) and the combined organic fractions were washed with 1M HCl (2×), sat. aq. NaHCO3 (2×), dried, and concentrated. The crude product was purified by flash chromatography (gradient 100% hexanes-60% EtOAc/hexanes) to afford 4.74 g of product as an oil (86%).

Provenance & Evidence