1,3-Dichloroacetone → HCID 23657702, compound

Participants

Reaction Steps

Dried K2CO3 (7g, 50.1 mmol) was added to a solution of 2-bromo-6-hydroxybenzaldehyde (80) (6.57 g, 32.3 mmol) in dry butanone (35 mL). The suspension was refluxed for 30 min and cooled to room temperature. A solution of 1,3-dichloroacetone (3 g, 24.23 mmol) in 5 mL of dry butanone was added. The reaction mixture was refluxed for 4 hours, cooled down, filtered through a pad of Celite (2 cm) and concentrated. A dark residue was recrystallized from CHCl3 to give 82 as brown solid (5.05 g, 76%): mp 223-225° C. 1H NMR (DMSO-d6) δ8.10 (s, 2H), 7.92 (d, J=8.2 Hz, 2H), 7.70 (d, J=7.7 Hz, 2H), 7.57 (dd, J=8.2, 7.7 Hz, 2H). HPLC (method B) tR 9.83 min (100.00 area %). Anal. (C17H8Br2O3) C, H, Br.

Provenance & Evidence