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Water → Ethyl 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoate

HRID 585325
Notes
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Reaction equation

HRID 585325 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].Br[CH2:22][C:23](=[O:26])[CH2:24][CH3:25].O>CN(C=O)C>[Br:7][C:8]1[C:18]([O:19][CH2:22][C:23]([CH2:24][CH3:25])=[O:26])=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 131561-Bromo-2-butanoneHCID 14851207Ethyl 2,4-dibromo-3-hydroxybenzoate

Product 1

HCID 22340637Ethyl 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

0.853 g (6.20 mmol) of K2CO3, 0.154 g (0.90 mmol) of KI and 1.000 g (3.10 mmol) of ethyl 2,4-dibromo-3-hydroxybenzoate were initially charged in 10 ml of DMF. At RT, 0.621 g (3.70 mmol) of 1-bromo-2-butanone was added, and the mixture was then heated at 80° C. for 4 h. The mixture was then poured into water and extracted with diisopropyl ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to dryness. Drying under oil pump vacuum gave ethyl 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoate as a brown oil.

Workup

  1. extractionextracted with diisopropyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customDrying under oil pump vacuum

Sources & evidence

ORD record
ord-0d5c6681367a462bbbad58a5349721f0
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06930208B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes