Dimethylformamide → 6-Bromo-2,2',4'-trifluoro-3-isopropoxybiphenyl-4-carbaldehyde

HRID 2272501Notes

Reaction equation

HRID 2272501 reaction equation
I[CH:2]([CH3:4])[CH3:3].[Br:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[C:10]([F:20])[C:9]([OH:21])=[C:8]([CH:22]=[O:23])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[C:10]([F:20])[C:9]([O:21][CH:2]([CH3:4])[CH3:3])=[C:8]([CH:22]=[O:23])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1179922396-Bromo-2,2',4'-trifluoro-3-hydroxybiphenyl-4-carbaldehyde

Product 1

HCID 1180381136-Bromo-2,2',4'-trifluoro-3-isopropoxybiphenyl-4-carbaldehydeYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Iodopropane (461 mg) was added at room temperature to a mixture of 6-bromo-2,2′,4′-trifluoro-3-hydroxybiphenyl-4-carbaldehyde (598 mg), potassium carbonate (499 mg), and DMF (10 mL), and the mixture was stirred at 60 C for 3 hours in a nitrogen atmosphere. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was separated, then 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 (637 mg).

Workup

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

Sources & evidence

ORD record
ord-095b663f32ca482497d8294705d965c1
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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