Dichloromethane → Ethyl 4-bromocinnamate

HRID 1590377Notes

Reaction equation

HRID 1590377 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH3:13])=[O:11].Cl[CH2:35]Cl>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:14][C:10]([O:12][CH2:13][CH3:35])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 707414-Bromobenzaldehyde

Product 1

HCID 141107Ethyl 4-bromocinnamate

Conditions

Temperature
25 °C

Procedure

4-Bromobenzaldehyde (9.25 g) was dissolved in dry dichloromethane (250 ml) at 25° C. under nitrogen. Carbomethoxymethylene triphenylphosphorane (17.4 g) (ex Lancaster) was added and the solution stirred at 25° C. for 18 hours. The solvent was removed under vacuum. The residue was washed with hexane and filtered. Removal of the hexane under vacuum gave ethyl 4-bromocinnamate (12.12 g). NMR 1H; 7.35 (5H,m), 6.38 (1H,d), 4.1(2H,q), 1.35(3H,t).

Workup

  1. customThe solvent was removed under vacuum
  2. washThe residue was washed with hexane
  3. filtrationfiltered
  4. customRemoval of the hexane under vacuum

Sources & evidence

ORD record
ord-866bb1633071428c9ef1d5f525a6610b
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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