Phenethyl bromide → HCID 18986892, compound

HRID 2397053Notes

Reaction equation

HRID 2397053 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 18986892HCID 18986892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

66.02 g of 5-bromosalicylaldehyde was dissolved in 260 ml of N,N-dimethylformamide. Then 113.35 g of anhydrous potassium carbonate and 111.71 ml of (2-bromoethyl)benzene were added thereto and the resulting mixture was stirred at room temperature for 38 hours. After evaporation of the solvent under reduced pressure, ethyl acetate and water were added to the residue and the mixture was separated. The organic layer was collected and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the residue was recrystallized from isopropanol to give 82.62 g of 5-bromo-2-(2-phenylethoxy)benzaldehyde. m.p. 79°-80° C.

Workup

  1. customAfter evaporation of the solvent under reduced pressure, ethyl acetate and water
  2. additionwere added to the residue
  3. customthe mixture was separated
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-4fd8e99ab8124773967ee4495436eaa7
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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