Pyridine → 2-Bromoethyl cinnamate

HRID 1745387Notes

Reaction equation

HRID 1745387 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:12][CH2:13][CH2:14][OH:15].N1C=CC=CC=1>C(C(C)=O)C>[C:1]([O:15][CH2:14][CH2:13][Br:12])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 108982-BromoethanolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 543970042-Bromoethyl cinnamateYield 86.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

35.3 g (0.212 mol) of cinnamic acid chloride and 100 mL of methyl ethyl ketone were placed in a reaction vessel and stirred under a nitrogen atmosphere. 28.2 g (0.225 mol) of 2-bromoethanol and 21 g of pyridine were dissolved in 100 mL of methyl ethyl ketone and added dropwise in the aforementioned reaction vessel. After completion of dropping, the solution was refluxed with stirring for 2 hours and cooled. Pyridine hydrochloride was precipitated, and then separated from the solution by filtration. The filtrate was concentrated and then dissolved in methylene chloride. The solution of methylene chloride was poured into a separating funnel and washed with water. Then the solution was dried with anhydrous sodium sulfate and concentrated. Thus 47 g of 2-bromoethyl cinnamate was obtained.

Workup

  1. additionadded dropwise in the aforementioned reaction vessel
  2. temperaturethe solution was refluxed
  3. stirringwith stirring for 2 hours
  4. temperaturecooled
  5. customPyridine hydrochloride was precipitated
  6. customseparated from the solution by filtration
  7. concentrationThe filtrate was concentrated
  8. dissolutiondissolved in methylene chloride
  9. additionThe solution of methylene chloride was poured into a separating funnel
  10. washwashed with water
  11. dry with materialThen the solution was dried with anhydrous sodium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-451421b6549c4440a4d8ee5f1c8c60c9
Source dataset
uspto-grants-2006_03
Patent number
US07019104B1

Reaction notes

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