Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 58683689, compound

HRID 1991052Notes

Reaction equation

HRID 1991052 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][O:12][C:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13](=[O:14])/[CH:15]=[CH:4]/[C:3]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 131547102-Bromo-4-chlorobenzaldehyde

Product 1

HCID 58683689HCID 58683689, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Bromo-4-chlorobenzaldehyde (Boegesoe, Klaus P. et al., J. Med. Chem. (1983), 26(7), 93547) (6.3g, 28.7 mmol) and methoxycarbonylmethylenetriphenylphosphor-ane (10.5 g, 31.6 mmol) were refluxed in toluene (143 ml) for 1 hour. The reaction mixture was cooled and purified via chromatography (SiO2, acetone/hexanes 5/95) to yield the title compound as colorless crystals (4.8 g, 61%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified via chromatography (SiO2, acetone/hexanes 5/95)

Sources & evidence

ORD record
ord-e9b7756e18f5432583e7b102d59e98b1
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

Loading…