Acetic Acid → HCID 86646540, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of Preparative Example 3, C4 (1.0 eq) and AgNO3(0.5 eq.) in H2O (0.15M) was added acetic acid (2.0 eq.). The mixture was heated to 50° C. and then a solution of conc. H2SO4(3.0 eq.) in H2O (0.5M) was added to the mixture. The temperature was then raised to 70° C. and a solution of ammonium persulfate (3.0 eq.) in H2O (0.5M) was added dropwise over 10 min. The reaction mixture was heated at 70-75° C. for a further 30 min. After cooling, the reaction mixture was adjusted to pH=7 with 32% ammonium hydroxide solution, and extracted with Et2O. The extracts were washed with brine, dried (Na2SO4) and the solvent was removed under reduced pressure. Crude product was purified by flash column chromatography on silica gel using 2-10% Et2O/Petroleum ether, the desired D1 as a yellow oil (87% yield). 1H-NMR (300 MHz, CDCl3, 300K) δ 2.66 (3H, s). MS (ES) C6H3Cl2F3N2 requires: 231; 233, found: 232; 234 (M+H)+.

Provenance & Evidence