Bromoacetyl bromide → HCID 86634685, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-phenylcyclohexyl)-acetic acid ethyl ester (10.0 g, 40.6 mmol) (patent WO2004 047755) in DCM (100 mL) at 0° C. is added AlCl3 (9.94 g, 74 mmol) portionwise. After it is stirred at −1.8° C. for 10 min, bromoacetyl bromide (3.59 mL, 40.6 mmol) is added dropwise over 2 min. The reaction mixture is allowed to stir at −1.8° C. for 2 h. It is then poured slowly to water/ice mixture (200 mL) and stirred for 30 min. The mixture is extracted with DCM (2×50 mL). The organic phase is separated and washed with NaHCO3 (3×100 mL), and brine (3×100 mL), dried with Na2SO4, concentrated and dried under high vacuum to give the title compound (12.8 g) as a yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.05-1.17 (m, 2H) 1.20 (t, J=8.00 Hz, 3H) 1.39-1.51 (m, 2H) 1.56-1.68 (m, 1H) 1.76-1.87 (m, 4H) 2.18 (d, J=4.29 Hz, 2H) 2.48 (td, J=12.32, 2.65 Hz, 1H) 4.08 (q, J=7.24 Hz, 2H) 4.35 (s, 2H) 7.25 (d, J=8.34 Hz, 2H) 7.85 (d, J=8.59 Hz, 2H).

Provenance & Evidence