Benzylamine → Tert.-butyl 4-benzylamino-2-methyl-benzoate

Participants

Reaction Steps

tert.-butyl 4-bromo-2-methyl-benzoate (12 g; 43.4 mmol), caesium carbonate (21.2 g, 65 mmol), palladium(II)-acetate (1 g, 4.45 mmol) and BINAP (2.37 g, 4.40 mmol) are suspended in 150 ml of toluene under a nitrogen atmosphere and stirred for 10 minutes at ambient temperature. Then benzylamine (5.7 ml, 52.1 mmol) is added dropwise and the mixture is heated to 100° C. for two days. The mixture is then cooled, filtered to remove undissolved matter and evaporated to dryness. The oily residue is purified by chromatography (silica gel, petroleum ether/ethyl acetate 98:2). White crystals are obtained.

Provenance & Evidence