Potassium Carbonate → HCID 67126223, compound

Participants

Reaction Conditions

Reaction Steps

6-methoxy-3-methyl-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (9.88 g, 30.7 mmol), 4-chlorophenylboronic acid (6.23 g, 39.9 mmol) and K2CO3 (12.7 g, 91.9 mmol) were combined in a mixture of toluene/ethanol/water (80 mL/40 mL/40 mL) at room temperature in a heavy walled pressure flask. Following sparging of the mixture with Ar for 30 minutes, PdCl2(dppf) (1.12 g, 1.53 mmol) was added in one portion and the flask was sealed and heated to 50° C. for 2.5 h. After returning to room temperature, the layers were separated and the aqueous layer was extracted with EtOAc and Hex (2×50 mL each). The combined organics were washed with brine, filtered through a pad of Celite, and dried over anhydrous MgSO4. The resulting solution was absorbed on silica gel in vacuo and purified via Yamazen column chromatography (0-15% EtOAc/Hex) to provide 7.7 g (88%) of the title compound as an amorphous white solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.32 (d, J=8 Hz, 2H); 7.26 (d, J=8 Hz, 2H); 6.87 (d, J=8.4 Hz, 1H); 6.57 (d, J=2.8 Hz, 1H); 6.62 (dd, J=8.4, 2.8 Hz, 1H); 5.74 (d, J=2.8 Hz, 1H); 3.79 (s, 3H); 2.81 (ABq, J=20.8, 12.4 Hz, 1H); 2.60 (m, 1H); 2.59 (ABq, J=8.4, 2.8 Hz, 1H); 1.14 (d, J=6.4 Hz, 3H).

Provenance & Evidence