Sodium Carbonate → Ethyl acetate hexane

Participants

Reaction Conditions

Reaction Steps

1-Bromo-2,3-dimethoxy-5-nitronaphthalene (1 g), 4-t-butylphenylboronic acid (685 mg, 1.2 eq.), Pd(PPh3)4 (370 mg, 0.1 eq.), and Na2CO3 (680 mg, 2 eq.) were combined in a flask with 20 mL dioxane and 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 20% EtOAc/hexane yielding product as a yellow solid (1.159 g, 99% yield). 1H NMR (400 MHz) (CDCl3) δ 8.18 (dd, J=8 Hz, J=4 Hz, 1H), 8.08 (s, 1H), 7.79-7.77 (m, 1H), 7.54 (dt, J=8 Hz, J=4 Hz, 2H), 7.30 (t, J=4 Hz, 1H), 7.28-7.27 (m, 2H), 3.99 (s, 3H), 3.58 (s, 3H), 1.34 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 155.05, 150.69, 147.53, 145.44, 132.89, 132.72, 131.97, 130.66, 130.06, 125.26, 123.59, 123.54 121.87, 102.16, 61.08, 55.91, 34.71, 31.43.

Provenance & Evidence