Ethyl bromoacetate → HCID 13343417, compound

Participants

Reaction Conditions

Reaction Steps

4-Hydroxyisophthalaldehyde (TCI America) (10.75 g, 71.6 mmol) in CH3CN (150 mL) was treated with K2CO3 (10.1 g, 1 eq.) and ethyl bromoacetate (8.0 mL, 1 eq.). The mixture was heated at 90° C. for 18 h, then cooled and concentrated under vacuum. The residue was partitioned between EtOAc and water. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude product was purified on the Combiflash system with a 220 g silica gel column, eluting with hexanes/EtOAc. The product was obtained as a white solid, 3.8 g. 1H NMR (CDCl3) 10.08 (s, 1H, CHO), 8.24 (m, 1H), 8.01 (m, 1H), 7.72 (d, 1H), 7.63 (m, 1H), 4.48 (q, 2H, OCH2), 1.44 (t, 3H, OCH2CH3); m/z 218.94 [M+H]+.

Provenance & Evidence