Dichloromethane → HCID 86716086, compound

Participants

Reaction Steps

A mixture of 4-bromo-2-fluoroaniline (6.53 g, 34.4 mmol), 2-phenylmalonic acid (7.43 g, 41.2 mmol), and POCl3 (31.9 mL, 344 mmol) was stirred at reflux (130° C. aluminum block temp) for 45 min. The resulting homogeneous dark solution was chilled on an ice bath, diluted with DCM (50 mL) and ice (100 mL), and stirred on the ice bath while 15 M NH4OH (30 mL) was added intermittently with swirling over ˜5 min (delayed exotherm). The aqueous layer was extracted with DCM (1×25 mL), and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was flash chromatographed with a 20% to 50% DCM/heptane gradient to provide the title compound as a light yellow solid.

Provenance & Evidence