Hydrochloric Acid → 2,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoic acid

HRID 133483Notes

Reaction equation

HRID 133483 reaction equation
[Br:1][C:2]1[C:12]([O:13][CH2:14][C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])=[C:11]([Br:24])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+].Cl>C1COCC1.O>[Br:1][C:2]1[C:12]([O:13][CH2:14][C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])=[C:11]([Br:24])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12115355ethyl 2,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoate

Product 1

HCID 121153562,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.24 g (2.70 mmol) of ethyl 2,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoate were dissolved in 10 ml of THF and 10 ml of H2O, and 0.117 g of NaOH was added. After stirring at RT for 12 h the mixture was admixed with 6 N HCl and extracted with CH2Cl2. Drying of the organic phase over Na2SO4 gave 2,4-dibromo-3-(N,N-di-n-propylaminocarbonylmethoxy)benzoic acid as a viscous colorless oil.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialDrying of the organic phase over Na2SO4

Sources & evidence

ORD record
ord-2fac132d2f5e4b9b897344f5d8d29eb1
Source dataset
uspto-grants-2008_06
Patent number
US07390827B2

Reaction notes

Loading…