Trifluoroacetic acid → HCID 18431279, compound

Participants

Reaction Steps

Under nitrogen, a 250 milliliter round bottom flask was charged with 1-bromo-4-(vinyloxy)benzene (6.97 grams, 35.0 millimoles, 1.00 equivalent), dioxane (50 milliliters), 4-bromophenol (6.67 grams, 38.5 millimoles, 1.10 equivalent), and a stir bar. Trifluoroacetic acid (1.21 milliliter, 15.75 millimoles, 0.45 equivalent) was added and the flask was equipped with a condenser while maintaining an inert atmosphere. The reaction mixture was heated to reflux overnight, allowed to cool, and quenched with triethylamine (2.00 milliliters). The mixture was separated via automated flash column chromatography using 220 grams Grace normal phase silica column (5% ethyl acetate in hexanes). Concentration gave the product in form of a colorless oil (9.69 grams, 26.0 millimoles, 74%). 1H NMR (400 MHz, CDCl3) δ 7.41-7.32 (m, 4H), 6.91-6.81 (m, 4H), 5.86 (q, J=5.3 Hz, 1H), 1.62 (dd, J=5.3, 0.4 Hz, 3H); 13C-NMR (101 MHz, CDCl3) δ 154.71, 132.46, 119.59, 115.19, 98.44, 20.10.

Provenance & Evidence