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

HRID 2272468Notes

Reaction equation

HRID 2272468 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-8f2bef57360c4cd0af5cfded09ea7419
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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