Morpholine → Methyl 3-methyl-4-morpholin-4-ylbenzoate

Participants

Reaction Steps

BINAP (0.67 g; 1.1 mmol; 0.05 eq.) and palladium acetate (0.24 g; 1.1 mmol; 0.05 eq.) were added to a suspension methyl 4-bromo-3-methylbenzoate (5 g; 21.8 mmol; 1 eq.), Cs2CO3 (10.65 g; 32.7 mmol; 1.5 eq.) and morpholine (2.3 g; 26 mmol; 1.2 eq.) in dioxane (100 mL) and the reaction mixture was refluxed for 15 hours. After filtration through a pad of CELITE, the solution was concentrated in vacuo and the residue purified by column chromatography (petroleum ether/ethyl acetate, 80/20) to afford the title compound (4.3 g, 84%) as a yellow solid.

Provenance & Evidence