Water → HCID 86595577, compound

HRID 1928923Notes

Reaction equation

HRID 1928923 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:19]=[O:20])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:14]([CH:19]=[O:20])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 86595577HCID 86595577, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 5-bromopentanoate (28.6 g) was added to a suspension of 4-bromo-2-formylphenol (25.0 g) and potassium carbonate (18.9 g) in DMF (100 ml), and the resulting solution was stirred at 50° C. overnight under a nitrogen atmosphere. The solution was allowed to cool. Water was added and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain yellow oil of ethyl 5-(4-bromo-2-formylphenoxy)pentanoate (40.9 g).

Workup

  1. temperatureto cool
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7c5ed091a9044b5cb5513c24c3e07770
Source dataset
uspto-grants-2012_05
Patent number
US08183273B2

Reaction notes

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