Allyl Alcohol → [4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester

Participants

Reaction Steps

[4-Amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]acetic acid (0.62 g, 1.56 mmol) was dissolved in allyl alcohol (15 mL, 0.1 M). This solution was treated with 7 drops of concentrated H2SO4 and stirred at room temperature for 48 h. The reaction was concentrated, redissolved in ethyl acetate, washed with H2O, saturated aq NaCl (3×), dried over Na2SO4 and filtered. The filtrate was treated with decolorizing charcoal, boiled for 10 minutes, cooled to room temperature, filtered and concentrated. The crude solid was recrystallized from heptane and ethyl acetate to give [4-amino-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid allyl ester as a light orange solid (0.13 g, 20%). 1H NMR (DMSO-d6, 300 MHz) δ 8.92 (br t, J=5.4 Hz, 1 H), 7.49–7.80 (m, 4 H), 6.84 (d, J=8.7 Hz, 1 H), 6.63 (br dd, J1=8.7 Hz, J2=2.7 Hz, 1 H), 5.95–5.79 (m, 1 H), 5.29 (br d, J=17.1 Hz, 1 H), 5.19 (br d, J=10.5 Hz, 1 H), 4.91 (br s, 1 H), 4.83 (br s, 2 H), 4.61 (br d, J=5.4 Hz, 1 H).

Provenance & Evidence