methyl 2-(2,6-difluorophenyl)acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2,6-difluorophenylacetate (2.141 g, 11.50 mmol), NBS (2.6 g, 14.61 mmol) and AIBN (0.057 g, 0.345 mmol) were taken up in CCl4 (45 mL). The reaction mixture was stirred at reflux for 18 hours. Additional NBS (1.433 g, 8.05 mmol) and AIBN (0.038 g, 0.230 mmol) were added and stirring at reflux continued for 24 hours. Room temperature was attained and the reaction mixture filtered through Celite, washing with DCM. The filtrate was concentrated in vacuo and the residue purified by MPLC (0-10% EtOAc-hexanes) to give methyl bromo(2,6-difluorophenyl)-acetate as a pale yellow oil. at reflux for 18 hours stirring at reflux Room temperature the reaction mixture filtered through Celite washing with DCM The filtrate was concentrated in vacuo the residue purified by MPLC (0-10% EtOAc-hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Difluorophenylacetic acid (2.61 g, 15.16 mmol) was taken up in THF (52 mL)/MeOH (13 mL). TMS-Diazomethane, 2 M in Et2O (8.5 mL, 17.00 mmol) was added and the resulting mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue purified by MPLC (2-20% EtOAc-hexanes) to give methyl 2,6-difluorophenylacetate as a colourless oil. The solvent was removed in vacuo the residue purified by MPLC (2-20% EtOAc-hexanes)