Potassium Carbonate → Ethyl acetate hexane

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(5-Bromonaphthalen-1-yl)methanol (150 mg), 2-methoxy-4-trifluoromethylphenylboronic acid (167 mg, 1.2 eq.), Pd(OAc)2 (14 mg, 0.1 eq.), Xphos (60 mg, 0.2 eq.), and K2CO3 (262 mg, 3 eq.) were combined in a flask with 5 mL dioxane and 1.6 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. for 2 hours. 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 35% EtOAc/hexane yielding product as a clear oil (55 mg, 86% yield). 1H NMR (400 MHz) (CDCl3) δ 8.24-8.22 (m, 1H), 7.64 (dd, J=8 Hz, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.51 (d, J=8 Hz, 1H), 7.45-7.37 (m, 4H), 7.29 (s, 1H), 5.22 (s, 2H), 3.76 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ157.45, 136.48, 136.27, 133.49, 132.21, 132.16, 131.47, 131.29, 131.15, 127.29, 126.61, 125.77, 125.48, 125.41, 123.88, 122.79, 117.44, 117.40, 107.72, 63.94, 55.76.

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