Dimethylformamide → Methyl 2-((4-bromophenoxy)methyl)benzoate

HRID 1515222Notes

Reaction equation

HRID 1515222 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.CN(C=O)C.Br[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]>O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 53995976Methyl 2-((4-bromophenoxy)methyl)benzoateYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (152 g, 1.1 mol) and 4-bromophenol (95.2 g, 550 mmol) were added to a DMF (500 mL) solution of methyl 2-bromomethylbenzoate (115 g, 500 mmol), and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the product was extracted with ethyl acetate. An organic layer was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate, and thereafter the solvents were distilled off under a reduced pressure. The residue was purified by column chromatography (hexane-toluene=1:1), to give 139 g (86%) of the captioned compound in the form of a colorless oily product.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washAn organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvents were distilled off under a reduced pressure
  5. customThe residue was purified by column chromatography (hexane-toluene=1:1)

Sources & evidence

ORD record
ord-dc49970a5b154fd68ae465807f7e546e
Source dataset
uspto-grants-2012_07
Patent number
US08222419B2

Reaction notes

Loading…