Sodium Methoxide → Methyl 4-bromo-5-fluoro-2-methoxybenzoate

HRID 508192Notes

Reaction equation

HRID 508192 reaction equation
[Br:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](F)[CH:3]=1.[CH3:14][O-:15].[Na+]>CN(C=O)C>[Br:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:15][CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 66887346Methyl 4-bromo-2,5-difluorobenzoate

Product 1

HCID 66886916Methyl 4-bromo-5-fluoro-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

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

Workup

  1. waitat rt for 30 min
  2. customwas then brought back to 0° C.
  3. customquenched with EtOAc and 1M HCl
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (Pentane/EtOAc=9:1)

Sources & evidence

ORD record
ord-13359075c949400f990f517dcbf7eff1
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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