Isopropylamine → 2-Isopropylamino-5-(trifluoromethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Isopropylamine (4.0 mL) was dissolved in THF (20 mL). This solution was cooled to 0° C. and n-butyllithium (2.5 M, 20 mL) was added. The reaction was stirred for 90 min and then transferred to a solution of 2-fluoro-5-(trifluoromethyl)benzoic acid (4.2 g) in THF (40 mL) at −78° C. This mixture was stirred for 15 min and then quenched with aqueous NH4Cl. The mixture was extracted with EtOAc (3×), and the organic layer was dried, filtered, and concentrated in vacuo. Flash chromatography of the resulting residue provided 2-isopropylamino-5-(trifluoromethyl)benzoic acid (2.4 g). MS found: (M+H)+=248.2.

Provenance & Evidence