Triethylamine → 1727-53-3

HRID 964051Notes

Reaction equation

HRID 964051 reaction equation
[Br:1][CH:2]([CH:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]C)=[O:4].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Br:1][C:2](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 245160Methyl 2,3-dibromo-3-phenylpropanoate

Product 1

HCID 2465851727-53-3

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 50 g of methyl 2,3-dibromo-3-phenylpropanoate, 100 ml of triethylamine and 500 ml of toluene is heated to boiling for 1 h and subsequently cooled to room temperature and filtered. The filtrate is evaporated in vacuo, and the α-bromocinnamic acid obtained in this way is used further without purification. 0.2 mol of the azol derivative dissolved in 150 ml of anhydrous DMF is added dropwise with stirring to a suspension of 4.7 g of NaK (80% in mineral oil) in 100 ml of anhydrous DMF. The temperature of the mixture is maintained below 35° C. during this by cooling with ice. After the addition is complete, the mixture is stirred at room temperature for 1 h. The previously prepared α-bromocinnamic acid is dissolved in 200 ml of anhydrous DMF and, while cooling with ice, the solution of the azol sodium salt is added dropwise with stirring. After stirring at room temperature for two hours, 10.8 ml of glacial acetic acid are added, the mixture is stirred into 1.5 l of ice-water and extracted several times with ethyl acetate, and the organic phases are washed with water. The organic phases are dried and evaporated in vacuo, and the residue is purified by column chromatography on silica gel (mobile phase: n-heptane/ethyl acetate) or recrystallization.

Workup

  1. temperatureis heated
  2. filtrationfiltered
  3. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-159b769ff4de4891b2fc224137aeff89
Source dataset
uspto-grants-1998_06
Patent number
US05767141

Reaction notes

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