Water → ethyl 2,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoate

HRID 133482Notes

Reaction equation

HRID 133482 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[C:18]([OH:19])=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:21]([N:24]([CH2:29][CH2:30][CH3:31])[C:25](=[O:28])[CH2:26]Cl)[CH2:22][CH3:23].O>CC(C)=O>[Br:7][C:8]1[C:18]([O:19][CH2:26][C:25]([N:24]([CH2:29][CH2:30][CH3:31])[CH2:21][CH2:22][CH3:23])=[O:28])=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2196472-chloro-N,N-dipropylacetamideHCID 14851207Ethyl 2,4-dibromo-3-hydroxybenzoate

Product 1

HCID 12115355ethyl 2,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.853 g of K2CO3, 0.154 g of KI and 1.000 g of ethyl 2,4-dibromo-3-hydroxybenzoate were introduced in 10 ml of acetone. At RT 0.783 g of N,N-di-n-propylchloroacetamide was added. The mixture was then heated at reflux for 4 hours. It was subsequently poured into water and extracted with diisopropyl ether. The organic phases were washed with water, dried over Na2SO4 and concentrated. Chromatography on silica gel (eluent: n-heptane/ethyl acetate) gave ethyl 2,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoate as brown oil.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 4 hours
  3. extractionextracted with diisopropyl ether
  4. washThe organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3b6a91e228640c28891b1a4045c92e2
Source dataset
uspto-grants-2008_06
Patent number
US07390827B2

Reaction notes

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