Pivaloyl chloride → 2-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(aminomethyl)-2-methylbenzoic acid hydrochloride (3.2 g, 14 mmol), BSTFA (2.26 mL, 14 mmol) and 50 mL THF was heated to reflux for 1 h and cooled to 0° C. 10 mL of TEA were added, followed by 1.77 mL (14 mmol) Piv-Cl in 50 mL THF. The mixture was stirred overnight at rt, concentrated i.vac., diluted with water and acidified with 22 mL glacial acetic acid. After 30 min it was extracted 3× with DCM, the organic phase was dried with Na2SO4, concentrated i.vac and purified via MPLC. Yield: 2.57 g (66%). MS [M+H]+=270 (Cl-isotope pattern); HPLC: Rt=4.09 min (Method MC-2).

Provenance & Evidence