Dibromoisocyanuric acid → 6-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehyde

HRID 531098Notes

Reaction equation

HRID 531098 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>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

4

Reactant 2

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

Product 1

HCID 904231046-Bromo-2,4'-difluoro-3-hydroxybiphenyl 4 carbaldehydeYield 122.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dibromoisocyanuric acid (24.8 g) was added to a solution of 2,4′-difluoro-3-hydroxybiphenyl-4-carbaldehyde (33.7 g) in DMF (400 mL) at room temperature. The mixture was stirred at the same temperature under nitrogen atmosphere for 3 hours. The mixture was quenched with aqueous saturated sodium thiosulfate solution at room temperature and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (33.1 g).

Workup

  1. customThe mixture was quenched with aqueous saturated sodium thiosulfate solution at room temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-346b1286334c4510bfdb1fbc41925d31
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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