(2,4-Dichlorophenoxy)Acetic Acid → Methyl 4-{[(2,4-dichlorophenoxy)acetyl]amino}benzoate

Participants

Reaction Steps

The mixture of (2,4-dichloro-phenoxy)-acetic acid (110.5 mg, 0.5 mmol), 4-aminobenzoic acid methyl ester (151.2 mg, 1.0 mmol), 4-dimethylaminopyridine (122.7 mg, 1.0 mmol) and benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (pybop) (520.3 mg, 1.0 mmol) in DMF (8.0 mL) was stirred overnight and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1) to give 4-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (169.6 mg, 95.8% yield).

Provenance & Evidence