Ethyl Acetate → 2-Bromo-4-chloro-1-[(2,2-diethoxyethyl)thio]benzene

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (0.926 g, 9.34 mmol) then bromoacetaldehyde dimethyl acetal (1.35 g, 6.85 mmol) were added to a solution of 2-bromo-4-chlorobenzenethiol (1.397 g, 6.23 mmol) in anhydrous DMF (11 mL). The mixture was heated at 70° C. for 3 hours. After being allowed to cool to room temperature, the mixture was diluted with ethyl acetate and water. The resulting layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organics were washed with water then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated. The resulting light yellow oil was used directly for the following step. 1H NMR (500 MHz, CDCl3) δ 7.57 (d, J=2.0 Hz, 1H); 7.33 (d, J=8.5 Hz, 1H); 7.26 (dd, J=8.5, 2.0 Hz, 1H); 4.70 (t, J=5.5 Hz, 1H); 3.75-3.68 (m, 2H); 3.61-3.55 (m, 2H); 3.15 (d, J=5.5 Hz, 2H); 1.23 (t, 7.0 Hz, 6H).

Provenance & Evidence