Acetic Acid → 1-(5-Iodopyridin-2-YL)cyclobutanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

1-(5-Iodo-pyridin-2-yl)-cyclobutane carbonitrile (4.0 g, 14 mmol) was combined with water (5.0 mL), glacial AcOH (5.0 mL) and concentrated sulfuric acid (5.0 mL). The homogeneous solution was heated to reflux (external bath: 115° C.). After 5 h, the solution was cooled to room temperature and poured into water (10 mL) and Et2O (15 mL). The layers were separated and the Et2O layer was discarded. The aqueous layer was adjusted to pH 4.5-5 by the addition of 2M aq. NaOH and then extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 layers were washed with brine, dried over MgSO4, filtered and concentrated to yield 3.92 g of 1-(5-iodo-pyridin-2-yl)-cyclobutane carboxylic acid, m/z 304.4 [M+H]+.

Provenance & Evidence