Dimethylformamide → Methyl 5-(benzyloxy)-2-bromo-2',4'-difluorobiphenyl-4-carboxylate

HRID 531074Notes

Reaction equation

HRID 531074 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.CN(C=O)C.[CH2:17]([O:24][C:25]1[CH:26]=[C:27]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2[F:42])[CH:28]=[CH:29][C:30]=1[C:31]([O:33][CH3:34])=[O:32])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:24][C:25]1[C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]([Br:1])=[C:27]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2[F:42])[CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 192912Dibromoisocyanuric acidHCID 117992142Methyl 3-(benzyloxy)-2',4'-difluorobiphenyl-4-carboxylate

Product 1

HCID 117992213Methyl 5-(benzyloxy)-2-bromo-2',4'-difluorobiphenyl-4-carboxylateYield 141.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibromoisocyanuric acid (15.9 g) was added at room temperature to a DMF (150 mL) solution of methyl 3-(benzyloxy)-2′,4′-difluorobiphenyl-4-carboxylate (28.0 g), and the mixture was stirred overnight at the same temperature as above. Water was added to the reaction mixture at room temperature, 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 (34.0 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-9a24129254124ee68ae64bbec05d2c46
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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