Bis(dimethylaminoethyl) ether → 1-(3,4-Dichlorophenyl)-1-propanone

Participants

Reaction Conditions

Reaction Steps

To a solution of THF (100 mL) and 2,2′-oxybis(N,N-dimethylethanamine) (9.18 g, 57.3 mmol) cooled to 0° C. was added ethylmagnesium bromide (19.1 mL, 57.3 mmol, 3N in THF) and stirred for 10 min. The solution was cooled to −60° C. and a solution of 3,4-dichlorobenzoyl chloride (10.0 g, 47.7 mmol) in THF (20 mL) was added dropwise over 10 min. The reaction was stirred for 1 h, quenched by adding sat'd. NH4Cl sat. and extracted with EtOAc. The combined extracts were dried with (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography (Biotage 40M) eluting an EtOAc/hexane gradient (2 to 10% EtOAc) to afford 6.0 g (85%, 53% pure) 1-(3,4-dichlorophenyl)propan-1-one (156) as clear oil which was used without additional purification.

Provenance & Evidence