3-Phenylprop-2-Enal → alpha-Bromocinnamaldehyde

HRID 555974

Reaction equation

HRID 555974 reaction equation
[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11]Br.C([O-])([O-])=O.[K+].[K+].O>C(O)(=O)C>[Br:11][C:2](=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:1]=[O:10]

Participants

6

Reactant 4

HCID 3073-Phenylprop-2-EnalHCID 962WaterHCID 11430Potassium CarbonateHCID 24408Bromine

Product 1

HCID 21585alpha-Bromocinnamaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.33 g (10 mmol) cinnamaldehyde was dissolved in 5 mL glacial acetic acid and cooled on an ice-water bath. 1.62 g bromine was added, and anhydrous K2CO3 was then added, and it was stirred until no gas was evolving. After refluxing for 30 min, the reaction mixture was poured into 100 mL cold water with stirring, extracted with 50 mL ethyl ether three times. The combined ethyl ether layers were washed with water one time, saturated aqueous NaCl solution one time, dried over MgSO4 for 2 hours, filtrated, and the filtrate was dried under vacuum, and washed with anhydrous ethyl ether: petroleum ether (1:1) to give the title compound as light yellow powder.

Workup

  1. temperaturecooled on an ice-water bath
  2. temperatureAfter refluxing for 30 min
  3. stirringwith stirring
  4. extractionextracted with 50 mL ethyl ether three times
  5. washThe combined ethyl ether layers were washed with water one time, saturated aqueous NaCl solution one time
  6. dry with materialdried over MgSO4 for 2 hours
  7. filtrationfiltrated
  8. customthe filtrate was dried under vacuum
  9. washwashed with anhydrous ethyl ether: petroleum ether (1:1)

Sources & evidence

ORD record
ord-33127781f18340369da56dfe4b8793c5
Source dataset
uspto-grants-2011_11
Patent number
US08053577B2

Linked notes

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