1,4-Dibromobenzene → 4-(4-Bromophenyl)morpholin-3-one

Participants

Reaction Conditions

Reaction Steps

A solution of 1,4-dibromobenzene (283 mg, 1.200 mmol), morpholin-3-one (101.104 mg, 1.000 mmol), dibasic potassium phosphate (348 mg, 2.000 mmol), copper (I) iodide (38.1 mg, 0.200 mmol) and N,N′-dimethylethylenediamine (0.043 ml, 0.400 mmol) in dioxane (3 ml) was purged with nitrogen for 2 min, sealed in a reaction vial and heated in a heating block at 105° C. for 15 h. The crude product mixture was filtered, and charged to a 12 g silica gel cartridge which was eluted with 0-50% EtOAc in hexanes to give the title compound (173 mg, 0.676 mmol, 67.6% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.56 (1H, none), 7.55 (2 H, d, J=8.80 Hz), 7.24 (2 H, d, J=8.58 Hz), 4.04 (2 H, dd, J=5.83, 4.29 Hz), 3.73-3.79 (2 H, m). HPLC (condition F): ret. Time 2.213 min; LC/MS [m/z, (M+H)] 258.0.

Provenance & Evidence