Ethyl 4-bromobutyrate → HCID 13558283, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl-4-bromobutyrate (190.7 g, 978 mM) was added with stirring to 2'-amino-4',5'-dimethoxyacetophenone (31.8 g, 163 mM) in triethylamine (33.9 mM) and the reaction mixture was heated at 110° C. for one hour. After cooling to room temperature 100 mL of 2% NaHCO3 was added and the reaction mixture was stirred for sixteen hours. A yellow solid formed which was dissolved in CHCl3 (250 mL). The aqueous phase was extracted with CHCl3 (4×200 mL), the organic extracts were combined and dried over MgSO4, filtered, and the solvent removed in vacuo to give a semisolid residue. The residue was chromatographed on SilicAR CC-7 and the appropriate fractions were crystallized upon standing from ether to afford the title compound in 62% yield, ,mp 74°-76° C.

Provenance & Evidence