Dimethylformamide → 6-Bromo-2,4'-difluoro-3-methoxybiphenyl-4-carbaldehyde

HRID 531136Notes

Reaction equation

HRID 531136 reaction equation
IC.[Br:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([F:17])[C:7]([OH:18])=[C:6]([CH:19]=[O:20])[CH:5]=1.[C:21](=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([F:17])[C:7]([O:18][CH3:21])=[C:6]([CH:19]=[O:20])[CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 904231046-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehyde

Product 1

HCID 1179923626-Bromo-2,4'-difluoro-3-methoxybiphenyl-4-carbaldehydeYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodomethane (1.35 g) was added at room temperature to a mixture of 6-bromo-2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (1.99 g), potassium carbonate (1.76 g), and DMF (40 mL), and the resultant mixture was stirred at 60° C. for 3 hours in a nitrogen atmosphere. Water was added to the reaction mixture at room temperature, 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. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (2.03 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated saline in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7afc7a4a673942158f23d372b7560a27
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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