Dimethylformamide → Methyl 2-bromo-2',4'-difluoro-5-isopropoxybiphenyl-4-carboxylate

HRID 2272487Notes

Reaction equation

HRID 2272487 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[C:22]([O:30][CH:31]([CH3:33])[CH3:32])[CH:21]=1.CN(C=O)C>O>[Br:1][C:25]1[CH:24]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[C:22]([O:30][CH:31]([CH3:33])[CH3:32])=[CH:21][C:20]=1[C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[F:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 117992133Methyl 2',4'-difluoro-3-isopropoxybiphenyl-4-carboxylate

Product 1

HCID 117992111Methyl 2-bromo-2',4'-difluoro-5-isopropoxybiphenyl-4-carboxylateYield 166.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibromoisocyanuric acid (2.19 g) was added to a mixture of methyl 2′,4′-difluoro-3-isopropoxybiphenyl-4-carboxylate (3.90 g) and DMF (40 mL), and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, 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 (4.90 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-09026bb9bccf42ca9f0dccda8bab1823
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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