Sodium Thiosulfate → 6-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehyde

HRID 531135Notes

Reaction equation

HRID 531135 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[F:12][C:13]1[C:18]([OH:19])=[C:17]([CH:20]=[O:21])[CH:16]=[CH:15][C:14]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Br:1][C:15]1[C:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[C:13]([F:12])[C:18]([OH:19])=[C:17]([CH:20]=[O:21])[CH:16]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 192912Dibromoisocyanuric acidHCID 904239512,4'-Difluoro-3-hydroxy-[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 904231046-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehydeYield 122.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dibromoisocyanuric acid (1.49 g) was added at room temperature to a DMF (50 mL) solution of 2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (2.02 g), and the mixture was stirred at the same temperature as above for 3 hours in a nitrogen atmosphere. A saturated aqueous solution of sodium thiosulfate 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 (1.99 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-44e016c5d39d4ab6a8f5913037987459
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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