Morpholine → HCID 59526391, compound

Participants

Reaction Steps

A sealed tube was charged with 1-bromo-3,5-difluorobenzene (1.79 ml, 15.5 mmol), Pd2(dba)3 (0.85 g, 0.93 mmol), X-PHOS (2.22 g, 4.66 mmol), and potassium carbonate (4.73 g, 34.2 mmol). The tube was evacuated and backfilled with argon 3×. Fully degassed tert-amyl alcohol (51 mL) was added followed immediately by the addition of morpholine (2.71 ml, 31.1 mmol). The tube was then sealed and placed in an oil bath at 100° C. and stirred overnight. The reaction mixture was taken up in diethyl ether and water. The aqueous layer was extracted twice with diethyl ether. The organics were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Purification via flash chromatography (silica, 0-17% diethylether/hexanes) afforded the title compound as a light yellow solid.

Provenance & Evidence