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

HRID 531067
Notes
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Reaction equation

HRID 531067 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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. The reaction mixture was cooled to room temperature, and then, the solvent was distilled off under reduced pressure. The obtained residue was diluted with ethyl acetate and water, followed by extraction with ethyl acetate. The obtained organic layer was 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. distillationthe solvent was distilled off under reduced pressure
  4. additionThe obtained residue was diluted with ethyl acetate and water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe obtained organic layer was washed with water and saturated saline in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1a30248d054a40ff97bf48a168611ffe
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09353108B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes