Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(3-bromophenyl)prop-2-enoate

HRID 1387906

Reaction equation

HRID 1387906 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][O:11][C:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:14][C:12]([O:11][CH3:10])=[O:13]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 765833-Bromobenzaldehyde

Product 1

HCID 610698Methyl 3-(3-bromophenyl)prop-2-enoateYield 82.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 3-bromobenzaldehyde (10 g) and methoxy-carbonylmethylenetriphenylphosphine (20 g) was added toluene (150 ml), and the mixture was refluxed under nitrogen atmosphere for 2 hours. The solvent was evaporated, and the organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give methyl 3-bromocinnamate (10.7 g) as colorless crystals. 1H-NMR(δ ppm, CDCl3): 3.82 (3H, s), 6.44 (1H, d, J=16.0 Hz),

Workup

  1. temperaturethe mixture was refluxed under nitrogen atmosphere for 2 hours
  2. customThe solvent was evaporated
  3. washthe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was purified with silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ea691ffa488b48a2ab23977a4fb9565f
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Linked notes

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