Sodium Methoxide → 4-Bromo-3-fluoro-2-methoxybenzaldehyde

HRID 2272524Notes

Reaction equation

HRID 2272524 reaction equation
[CH3:1][O-:2].[Na+].[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7](F)[C:6]=1[F:14]>CO>[Br:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([O:2][CH3:1])[C:6]=1[F:14]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 269863904-Bromo-2,3-difluorobenzaldehyde

Product 1

HCID 840385064-Bromo-3-fluoro-2-methoxybenzaldehydeYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (28% methanol solution, 69.1 g) was added to a solution of 4-bromo-2,3-difluorobenzaldehyde (52.8 g) in methanol (600 mL) at room temperature. The mixture was refluxed under nitrogen atmosphere for 2 hours and concentrated in vacuo to about ¼ volume. The mixture was diluted with ethyl acetate and water. The mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (52.3 g).

Workup

  1. temperatureThe mixture was refluxed under nitrogen atmosphere for 2 hours
  2. concentrationconcentrated in vacuo to about ¼ volume
  3. additionThe mixture was diluted with ethyl acetate and water
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98938789cffe45858e816bdfa091daec
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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