Dimethylformamide → Methyl 2-bromo-5-ethoxy-4'-fluorobiphenyl-4-carboxylate

HRID 530984Notes

Reaction equation

HRID 530984 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:18]=[CH:19][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:13].CN(C=O)C>O>[Br:1][C:18]1[CH:19]=[C:20]([C:21]([O:23][CH3:24])=[O:22])[C:15]([O:14][CH2:12][CH3:13])=[CH:16][C:17]=1[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 117992167Methyl 3-ethoxy-4'-fluorobiphenyl-4-carboxylate

Product 1

HCID 117992268Methyl 2-bromo-5-ethoxy-4'-fluorobiphenyl-4-carboxylateYield 188.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibromoisocyanuric acid (3.28 g) was added to a mixture of methyl 3-ethoxy-4′-fluorobiphenyl-4-carboxylate (5.92 g) and DMF (40 mL), and the resultant mixture was stirred overnight at room temperature. Water was added to the reaction mixture at room temperature, 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 (7.62 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-cd94e7e9f73b4d20992179707d3be51a
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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