Butyl bromide → HCID 66619669, compound

Participants

Reaction Conditions

Reaction Steps

4-[3-(Aminocarbonyl)-2,4-difluorophenoxy]-2-butenoic acid, mixture of isomeres (3:2) E:Z, (526 mg, 2 mmol, 1 equiv.) was dissolved in dry DMF (5 ml). K2CO3 (850 mg, 6 mmol, 3 equiv.) and n-butylbromide (0.23 ml, 2.1 mmol, 1.05 equiv.) were added and the reaction mixture was heated for 70 h at 50° C. and for 1.5 h at r.t. After cooling at r.t., the mixture was diluted with H2O (50 ml) and extracted with EtOAc (3×40 ml). The combined organic extracts were washed with H2O (6×30 ml), dried (MgSO4) and evaporated to dryness under reduced pressure. The oily residue was purified by column chromatography on silica, eluted with CH2Cl2 and MeOH/CH2Cl2 (1%), to give 364 mg, 57% yield, mp<40° C. HPLC-MS (method 1): m/z 314 [M+H]+, Rt=3.88 min. By 1H-NMR analysis it was determined to be a mixture of isomeres in a ratio (5:7) E:Z. When the same reaction was performed on the acid (3:40) E:Z mixture of isomeres, the product obtained was determined to be a mixture of isomeres in a ratio (1:4) E:Z.

Provenance & Evidence