Sodium Methoxide → 2,2',4'-Trifluoro-3-methoxybiphenyl-4-carbaldehyde

HRID 2272498Notes

Reaction equation

HRID 2272498 reaction equation
[CH3:1][O-:2].[Na+].[F:4][C:5]1[C:10](F)=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21]>CO>[F:4][C:5]1[C:10]([O:2][CH3:1])=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 1179922312,2',3,4'-Tetrafluoro-[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 1179920892,2',4'-Trifluoro-3-methoxybiphenyl-4-carbaldehydeYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (28% methanol solution, 5.64 g) was added at room temperature to a methanol (120 mL) solution of 2,2′,3,4′-tetrafluorobiphenyl-4-carbaldehyde (4.95 g), and the mixture was heated to reflux for 16 hours in a nitrogen atmosphere. Then, the solvent was distilled off under reduced pressure. The residue was diluted with ethyl acetate and water, followed by extraction with ethyl acetate. The organic layer was separated, washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (5.14 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 hours in a nitrogen atmosphere
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. additionThe residue was diluted with ethyl acetate and water
  5. extractionfollowed by extraction with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water and saturated saline in this order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ea26e10fd608429a9e1a59ade20c20ec
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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