Sodium Acetate → {[2,4-bis(methyloxy)phenyl]methyl}-3-bromo-4-methyl-1H-pyrrole-2,5-dione

HRID 1513335Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:9])O[C:5](=[O:8])[C:6]=1[CH3:7].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[CH2:20][NH2:21].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[CH2:20][N:21]1[C:5](=[O:8])[C:6]([CH3:7])=[C:2]([Br:1])[C:3]1=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

3-bromo-4-methyl-2,5-furandione (prepared as described in Org. and Bimolecular chemistry, pag 1782, 2004; 4.8 g, 25.1 mmol) and {[2,4-bis(methyloxy)phenyl]methyl}amine (3.78 mL, 25.1 mmol) were dissolved in acetic acid (100 mL) and the mixture was stirred at 100° C. overnight. Solvent was then concentrated under reduced pressure, additional acetic acid (100 mL) was added followed by sodium acetate (1.443 g, 17.59 mmol) and the mixture was refluxed for further 3 hours. Solvent was eliminated under reduced pressure and the residue was partitioned between DCM and water. Organic phase was washed with water, dried and solvent was eliminated under reduced pressure providing a crude that was purified by flash chromatography (eluent: Cy to Cy/AcOEt 7:3) affording 1-{[2,4-bis(methyloxy)phenyl]methyl}-3-bromo-4-methyl-1H-pyrrole-2,5-dione (8.55 g, 25.1 mmol, 100% yield) as a light yellow solid.

Workup

concentrationSolvent was then concentrated under reduced pressure, additional acetic acid (100 mL)
additionwas added
temperaturethe mixture was refluxed for further 3 hours
customthe residue was partitioned between DCM and water
washOrganic phase was washed with water
customdried
customproviding a crude that
customwas purified by flash chromatography (eluent: Cy to Cy/AcOEt 7:3)

Sources & evidence

ORD record: ord-8d0ca8ad3408404eaf3c42458d12c6fe
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217168B2

Reaction notes

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