3-bromoprop-1-en-2-ylbenzene

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: α-(Bromomethyl)styrene was treated with an equimolar ratio of triethylphosphite at reflux for 1 h. After the mixture was cooled to room temperature, the by-product, ethyl bromide, was removed under reduced pressure, and the product α-(diethoxyphosphorylmethyl)styrene was obtained in quantitative yield as a yellowish syrup: 1H NMR (CDCl3) δ 1.20 (6H, t, 2× OCH2CH3, J 7.5 Hz), 3.05 (2H, d, CH2P(O), J 22.5 Hz), 4.00 (4H, m, 2× OCH2CH3), 5.35 (1H, d, olefinic proton, J 6.0 Hz), 5.50 (1H, d, olefinic proton, J 6 Hz), 7.25-7.55 (5H, m, aromatic protons). at reflux for 1 h the by-product, ethyl bromide, was removed under reduced pressure

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

Procedure: A mixture of 60 g of potassium phthalimide and 66.4 g of α-bromomethyl styrene (prepared by the method of S. F. Reed, Jr., J. Org. Chem., 30, 3258 (1965)) in 150 ml of dimethylformamide is refluxed for 2 hours, cooled, and diluted with 400 ml of water. The resulting solid is filtered and dried in vacuo to give 83.4 g of N-(2-phenyl-2-propenyl)phthalimide. A small sample that is recrystallized from acetone-hexane has a melting point of 118°-121°C. prepared by the method of S cooled The resulting solid is filtered dried in vacuo

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

Procedure: A mixture of 60 g of potassium phthalimide and 66.4 g of α-bromomethyl styrene (prepared by the method of S. F. Reed, Jr., J. Org. Chem., 30, 3258 (1965)) in 150 ml of dimethylformamide is refluxed for 2 hours, cooled, and diluted with 400 ml of water. The resulting solid is filtered and dried in vacuo to give 83.4 g of N-(2-phenyl-2-propenyl)phthalimide. A small sample that is recrystallized from acetone-hexane has a melting point of 118°-121°C. prepared by the method of S cooled The resulting solid is filtered dried in vacuo

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

Procedure: To a mixture of 2.30 g of 4-cyano-N-methylbenzenesulfonamide, 2.40 g of α-(bromomethyl)styrene and 20 ml of N,N-dimethylformamide, 0.63 g of 50% sodium hydride (oil dispersed) was slowly added with stirring under ice cooling, then the mixture was stirred at room temperature for 6 hours. After evaporating the solvent under a reduced pressure, ethyl acetate was added to the residue. The organic layer was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate n-hexane) to obtain 1.70 g of the titled compound. was slowly added the mixture was stirred at room temperature for 6 hours After evaporating the solvent under a reduced pressure, ethyl acetate was added to the residue The organic layer was washed with water dried over anhydrous sodium sulfate After distilling off the solvent the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate n-hexane)

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

Procedure: To a mixture of 2.30 g of 4-cyano-N-methylbenzenesulfonamide, 2.40 g of α-(bromomethyl)styrene and 20 ml of N,N-dimethylformamide, 0.63 g of 50% sodium hydride (oil dispersed) was slowly added with stirring under ice cooling, then the mixture was stirred at room temperature for 6 hours. After evaporating the solvent under a reduced pressure, ethyl acetate was added to the residue. The organic layer was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate n-hexane) to obtain 1.70 g of the titled compound. was slowly added the mixture was stirred at room temperature for 6 hours After evaporating the solvent under a reduced pressure, ethyl acetate was added to the residue The organic layer was washed with water dried over anhydrous sodium sulfate After distilling off the solvent the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate n-hexane)

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

Procedure: A mixture of 60 g of potassium phthalimide and 66.4 g of α-bromomethyl styrene (prepared by the method of S. F. Reed, Jr., J. Org. Chem., 30, 3258 (1965)) in 150 ml of dimethylformamide is refluxed for 2 hours, cooled, and diluted with 400 ml of water. The resulting solid is filtered and dried in vacuo to give 83.4 g of N-(2-phenyl-2-propenyl)phthalimide. A small sample that is recrystallized from acetone-hexane has a melting point of 118°-121°C. prepared by the method of S cooled The resulting solid is filtered dried in vacuo

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

Procedure: 6.72 g (0.28 mmol) of sodium hydride are dissolved in 660 ml of ether and 120 ml of dimethylformamide under argon, and 64.1 g (0.26 mol) of 3-hydroxy-2-iodobenzaldehyde in 65 ml of ether are slowly added. After the mixture has been stirred at room temperature for 15 minutes, 61 g (0.28 mol) of 3-bromo-2-phenyl-1-propene, dissolved in 60 ml of ether, are added dropwise and the mixture is stirred overnight. are added dropwise the mixture is stirred overnight

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

Procedure: 6.72 g (0.28 mmol) of sodium hydride are dissolved in 660 ml of ether and 120 ml of dimethylformamide under argon, and 64.1 g (0.26 mol) of 3-hydroxy-2-iodobenzaldehyde in 65 ml of ether are slowly added. After the mixture has been stirred at room temperature for 15 minutes, 61 g (0.28 mol) of 3-bromo-2-phenyl-1-propene, dissolved in 60 ml of ether, are added dropwise and the mixture is stirred overnight. are added dropwise the mixture is stirred overnight

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

Procedure: α-(Bromomethyl)styrene was treated with an equimolar ratio of triethylphosphite at reflux for 1 h. After the mixture was cooled to room temperature, the by-product, ethyl bromide, was removed under reduced pressure, and the product α-(diethoxyphosphorylmethyl)styrene was obtained in quantitative yield as a yellowish syrup: 1H NMR (CDCl3) δ 1.20 (6H, t, 2× OCH2CH3, J 7.5 Hz), 3.05 (2H, d, CH2P(O), J 22.5 Hz), 4.00 (4H, m, 2× OCH2CH3), 5.35 (1H, d, olefinic proton, J 6.0 Hz), 5.50 (1H, d, olefinic proton, J 6 Hz), 7.25-7.55 (5H, m, aromatic protons). at reflux for 1 h the by-product, ethyl bromide, was removed under reduced pressure