Propargyl bromide → Methyl 4-fluoro-3-(prop-2-yn-1-yloxy)benzoate

Participants

Reaction Steps

Methyl 4-fluoro-3-hydroxybenzoate (20.0 mL, 0.118 mol) was dissolved in anhydrous acetone (450 mL), mixed with propargyl bromide (26.2 g, 0.177 mol) followed by the addition of powdered K2CO3 (32.4 g, 0.236 mol) and the reaction mixture was stirred overnight at room temperature. The reaction was filtered and the solvent was removed in vacuo. The residue was dissolved in diethyl ether, washed 4 times with H2O, treated with brine, dried with MgSO4, filtered, and the solvent was removed in vacuo to give 25.5 g (100% yield) of a light peach coloured solid as the title compound (mp 60.5-61.5° C.). Mass spectrum (70 eV) m/z (relative intensity) 208 (27, M+), 207 (100), 193 (22), 177 (20), 149 (50), 82 (21), 81 (10).

Provenance & Evidence