Potassium Carbonate → Ethyl acetate hexane

Participants

Reaction Conditions

Reaction Steps

(5-Bromonaphthalen-1-yl)methanol (165 mg), 2-methyl-4-trifluoromethylphenylboronic acid (170 mg, 1.2 eq.), Pd(PPh3)4 (80 mg, 0.1 eq.), and K2CO3 (288 mg, 3 eq.) were combined in a flask with 5 mL dioxane and 2.5 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. overnight. Solution was cooled to room temperature then diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as a yellow oil (208 mg, 95% yield). 1H NMR (400 MHz) (CDCl3) δ 8.24 (d, J=8 Hz, 1H), 7.65-7.64 (m, 1H), 7.63-7.56 (m, 2H), 7.40-7.36 (m, 5H), 5.23 (s, 2H), 2.10 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ144.16, 139.06, 137.81, 136.68, 131.92, 131.42, 130.74, 126.63, 126.51, 126.20, 125.82, 125.56, 123.73, 122.52, 122.48, 63.84, 20.06.

Provenance & Evidence