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

HRID 531095Notes

Reaction equation

HRID 531095 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 1/4 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 1/4 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-e63fd325b17d4402ac6a29ae55c97372
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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