2-Propenoicacid, 3-[4-(bromomethyl)phenyl]-, methyl ester, (E)- (9CI)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.0 g (5.15 g) of 2,4-dihydroxy-3-propylacetophenone, 1.58 g (6.18 mmol) of methyl 4-bromomethylcinnamate and 0.85 g (6.18 mmol) of anhydrous potassium carbonate in 20 ml of acetone was stirred at reflux for 18 hours. Ether extraction gave 1.01 g of the title compound as a light yellow powder mp 121°-125° C. at reflux for 18 hours Ether extraction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.0 g (5.15 g) of 2,4-dihydroxy-3-propylacetophenone, 1.58 g (6.18 mmol) of methyl 4-bromomethylcinnamate and 0.85 g (6.18 mmol) of anhydrous potassium carbonate in 20 ml of acetone was stirred at reflux for 18 hours. Ether extraction gave 1.01 g of the title compound as a light yellow powder mp 121°-125° C. at reflux for 18 hours Ether extraction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3.0 g (17.03 mmol) of methyl 4-methylcinnamate, 3.33 g (18.73 mmol) of N-bromosuccinimide and 60 mg of 2,2'-azobis(2-methylpropionitrile) in 75 ml of carbon tetrachloride was heated to reflux with a heat lamp and stirred rapidly for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated to give the title compound as an oil which crystallized. NMR in CDCl3 (δ units): 3.80 (singlet, 3); 4.48 (singlet, 2); 6.44 and 7.67 (doublets, J=15 Hz, 1); 7.39, 7.49 (doublets, J=7 Hz, 2). was heated to reflux with a heat lamp filtered The filtrate was evaporated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5 ml of dry acetonitrile were added 1.4 g of 1-ethoxycarbonylimidazole and 2.55 g of methyl 4-bromomethylcinnamate, the mixture was stirred for 5 hours at room temperature. The precipitated crystals were collected by filtration and recrystallized from acetonitrile/diethyl ether to yield 2.9 g of 1-ethoxycarbonyl-3-[4-(2-methoxycarbonylvinyl)benzyl]imidazolium bromide. The precipitated crystals were collected by filtration recrystallized from acetonitrile/diethyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 5 ml of dry acetonitrile were added 1.7 g of 1-benzoylimidazole and 2.6 g of methyl 4-bromomethylcinnamate, and the mixture was stirred for 5 hours at room temperature. The precipitated crystals were collected by filtration and recrystallized from acetonitrile/diethyl ether to yield 3.5 g of 1-benzoyl-3-[4-(2-methoxycarbonylvinyl)benzyl]imidazolium bromide. The precipitated crystals were collected by filtration recrystallized from acetonitrile/diethyl ether