Triethylamine → HCID 59829174, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 1-(3,5-dibromo-4-(4-methoxybenzyloxy)phenyl)prop-2-en-1-one (E) (0.1003 g, 0.235 mmol) in ethanol (2 mL) was added hydrazine monohydrate (19.4 μL, 0.400 mmol) and the mixture was heated at 85° C. for 1 h. After cooling, the mixture was partitioned between dichloromethane (15 mL) and water (10 mL). The aqueous layer was extracted further with dichloromethane (15 mL) and the combined organic extracts were washed with brine (10 mL), dried (Na2SO4), and nitrogen was bubbled through the solution for a few minutes. The solution was concentrated to 10 mL in vacuo with no heat and then added by syringe to a stirred mixture of 3-bromo-4-chlorobenzoyl chloride (59.8 mg, 0.236 mmol) in dichloromethane (1 mL) under nitrogen. Triethylamine (34.4 μL, 0.247 mmol) was then added dropwise and the resulting solution was stirred at room temperature for 64 h. The mixture was diluted with dichloromethane (10 mL) and successively washed with water (10 mL), 10% aqueous citric acid (10 mL), 1 N aqueous NaOH (10 mL), water (10 mL) and brine (10 mL). The remaining organic layer was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (silica gel, 40% EtOAc/pet. ether) to give 54.1 mg (35%) of the title compound as a yellow solid. 1H NMR δ (ppm) (CDCl3): 3.23 (2 H, t, J=10.04 Hz), 3.83 (3 H, s), 4.26 (2 H, t, J=10.05 Hz), 5.02 (2 H, s), 6.93 (2 H, d, J=8.32 Hz), 7.51 (2 H, d, J=8.18 Hz), 7.55 (1 H, d, J=8.38 Hz), 7.83 (2 H, s), 7.86 (1 H, dd, J=8.43, 2.07 Hz), 8.28 (1 H, d, J=2.02 Hz).

Provenance & Evidence