Reaktion #595374

ord-13359075c949400f990f517dcbf7eff1

Reaktionsgleichung

COC(=O)c1cc(F)c(Br)cc1F
methyl 4-bromo-2,5-difluorobenzoate
C[O-].[Na+]
NaOMe
COC(=O)c1cc(F)c(Br)cc1OC
title compound
COC(=O)c1cc(F)c(Br)cc1OC
methyl 4-bromo-5-fluoro-2-methoxybenzoate

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITat rt for 30 min
  2. 2
    Sonstigewas then brought back to 0° C.
  3. 3
    Sonstigequenched with EtOAc and 1M HCl
  4. 4
    SonstigeThe organic layer was separated
  5. 5
    Extraktionthe aqueous phase was extracted with EtOAc
  6. 6
    Trocknendried over Na2SO4
  7. 7
    Einengenconcentrated
  8. 8
    Sonstigepurified by flash chromatography (Pentane/EtOAc=9:1)

Vorschrift

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

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09095583B2uspto-grants-2015_08