Phenethyl bromide → 5-Chloro-2-(2-phenylethoxy)benzaldehyde

HRID 2397054Notes

Reaction equation

HRID 2397054 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 189868805-Chloro-2-(2-phenylethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 g of 5-chlorosalicylaldehyde was dissolved in 300 ml of acetonitrile. After adding 41.48 g of potassium fluoride/alumina (neutral) (2:3) and 17.45 ml of (2-bromoethyl)benzene, the resulting mixture was stirred at room temperature for 63 hours. Then the potassium fluoride/alumina was removed by filtration under sucking and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=10:1) and recrystallized from isopropyl ether to give 5.58 g of 5-chloro-2-(2-phenylethoxy)benzaldehyde.

Workup

  1. customThen the potassium fluoride/alumina was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=10:1)
  4. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-8f86f6282e874c0281feba95f40f1f40
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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