Ammonium Chloride → HCID 58579838, compound

Participants

Reaction Steps

To a solution of 2-(4-bromo-2-methoxyphenoxy)-N-methoxy-N-methylacetamide Part A (2 g, 6.58 mmol) in THF (25 mL) was slowly added cyclopropylmagnesium bromide (39.5 mL, 19.73 mmol). After stirring for 1 hour at RT, the reaction mixture was added to a sat. NH4Cl solution which was subsequently extracted with EtOAc, dried (Na2SO4), and concentrated. The crude product was purified using ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4-bromo-2-methoxyphenoxy)-1-cyclopropylethanone 16B (1.72 g, 6.03 mmol, 92% yield) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ 7.01 (2H, dddd), 6.65 (1H, d, J=8.53 Hz), 4.72 (2H, s), 3.89 (3H, s), 2.24-2.35 (1H, m), 1.15 (2H, quin, J=3.83 Hz), 0.98 (2H, dq, J=7.56, 3.67 Hz).

Provenance & Evidence