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Dimethylformamide → 6-Bromo-3-ethoxy-2,2',4'-trifluorobiphenyl-4-carbaldehyde

HRID 2272514
Notes
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Reaction equation

HRID 2272514 reaction equation
I[CH2:2][CH3:3].[Br:4][C:5]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[C:9]([F:19])[C:8]([OH:20])=[C:7]([CH:21]=[O:22])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:4][C:5]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[C:9]([F:19])[C:8]([O:20][CH2:2][CH3:3])=[C:7]([CH:21]=[O:22])[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1179922396-Bromo-2,2',4'-trifluoro-3-hydroxybiphenyl-4-carbaldehyde

Product 1

HCID 1180379856-Bromo-3-ethoxy-2,2',4'-trifluorobiphenyl-4-carbaldehydeYield 90.5%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Iodoethane (0.77 g) was added at room temperature to a mixture of 6-bromo-2,2′,4′-trifluoro-3-hydroxybiphenyl-4-carbaldehyde (1.09 g), potassium carbonate (0.91 g), and DMF (20 mL), and the mixture was stirred at 60 C for 2 hours in a nitrogen atmosphere. Water was added to the reaction mixture at room temperature, 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. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.07 g).

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-0ec9e0c92d6948758fe3f4973fd19086
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120777B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes