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

HRID 531133Notes

Reaction equation

HRID 531133 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][CH:15]=1>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][CH:15]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 871189052,3,4'-Trifluorobiphenyl-4-carbaldehyde

Product 1

HCID 904236032,4'-Difluoro-3-methoxybiphenyl-4-carbaldehydeYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (28% methanol solution, 7.37 g) was added at room temperature to a methanol (160 mL) solution of 2,3,4′-trifluorobiphenyl-4-carbaldehyde (6.01 g), and the mixture was heated to reflux for 18 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 (6.18 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 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-288287b07c964d23b19495b95ba3b036
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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