1,2-Dibromoethane → HCID 66920480, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of zinc (176 mg, 2.69 mmol) in dry THF (1 ml) in a dry flask under argon was added 1,2-dibromoethane (5.79 μl, 67.2 μmol). The mixture was heated three times to reflux with a heat-gun. After 5 min the flask was placed in an ice bath and a solution of 2-chloro-5-fluoro-benzylbromide (182 μl, 1.34 mmol) in dry THF (1.5 ml) was added slowly, so that the temperature remained at 0° C. The mixture was stirred at 0° C. for 3 h. Then the cooled suspension was added dropwise to a precooled solution (0° C.) of the compound of example 16, step 1 (59.0 mg, 134 μmol), nickel acetylacetonate (3.44 mg, 13.4 μmol) and tetrabutylammonium iodide (149 mg, 402 μmol) in THF (4 ml) and NMP (2 ml). The reaction mixture was stirred at 0° C. for 3 h and then at room temperature for 48 h. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative HPLC. The eluate was lyophilized overnight to give 17 mg of the title compound.

Provenance & Evidence