Dimethylformamide → Methyl 2-bromo-4'-fluoro-5-isopropoxy-[1,1'-biphenyl]-4-carboxylate

HRID 531001Notes

Reaction equation

HRID 531001 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[C:21]([O:29][CH:30]([CH3:32])[CH3:31])[CH:20]=2)=[CH:15][CH:14]=1.CN(C=O)C>O>[Br:1][C:24]1[CH:23]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:29][CH:30]([CH3:32])[CH3:31])=[CH:20][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 117992325Methyl 4'-fluoro-3-isopropoxybiphenyl-4-carboxylate

Product 1

HCID 117992274Methyl 2-bromo-4'-fluoro-5-isopropoxy-[1,1'-biphenyl]-4-carboxylateYield 127.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibromoisocyanuric acid (4.60 g) was added to a mixture of methyl 4′-fluoro-3-isopropoxybiphenyl-4-carboxylate (6.61 g) and DMF (60 mL), and the resultant mixture was stirred at room temperature for 5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline 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 (7.53 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with saturated saline
  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-8e514bd6613b4ad8b90595d05459b622
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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