Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 54041425, compound

HRID 1590396Notes

Reaction equation

HRID 1590396 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Br:10])[CH:5]=O.[C:11]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:13][CH2:14][CH3:15])=[O:12]>ClCCl>[CH2:14]([O:13][C:11](=[O:12])[CH:16]=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([Br:10])=[C:2]([Br:1])[CH:3]=1)[CH3:15]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 6220533,4-Dibromobenzaldehyde

Product 1

HCID 54041425HCID 54041425, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above aldehyde (2.25 g) was dissolved in dichloromethane (25 ml) and carboethoxymethylenetriphenylphosphorane (2.96 g) was added. After 18 hours at 25° the solution was concentrated in vacuo and the residue washed with hexane. Combined hexane washings were concentrated in vacuo to give ethyl-3-(3,4-dibromophenyl)propenoate (2.4 g). NMR 1H 7.7(2H,m), 7.50(1H,d), 7.15(1H,dd), 6.32(1H,d), 4.26(2H,q), 1.33(3H,t).

Workup

  1. concentrationAfter 18 hours at 25° the solution was concentrated in vacuo
  2. washthe residue washed with hexane
  3. concentrationCombined hexane washings were concentrated in vacuo

Sources & evidence

ORD record
ord-722dc59be7fa4d908e1363cad2046cbc
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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