Reaction #595374

Reaction equation

methyl 4-bromo-2,5-difluorobenzoate

NaOMe

→

title compound

methyl 4-bromo-5-fluoro-2-methoxybenzoate

Solvents

DMF

Conditions

Workup

1. 1
   workup.WAITat rt for 30 min
2. 2
   Otherwas then brought back to 0° C.
3. 3
   Otherquenched with EtOAc and 1M HCl
4. 4
   OtherThe organic layer was separated
5. 5
   Extractionthe aqueous phase was extracted with EtOAc
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated
8. 8
   Otherpurified by flash chromatography (Pentane/EtOAc=9:1)

Procedure

To a solution of methyl 4-bromo-2,5-difluorobenzoate (i-7c) (0.5 g, 2 mmol) in DMF (5 mL) at 0° C. was added NaOMe (25% in MeOH, 0.45 mL, 2 mmol). The reaction mixture was stirred at 0° C. for 10 min and then at rt for 30 min. The mixture was then brought back to 0° C. and quenched with EtOAc and 1M HCl. The organic layer was separated, and the aqueous phase was extracted with EtOAc, dried over Na2SO4, concentrated and purified by flash chromatography (Pentane/EtOAc=9:1) to give the title compound. LCMS (ESI) calc'd for C9H8BrFO3 [M+H]+: 263. found: 263

Source