[(Z)-2-bromoethenyl]benzene

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

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

Procedure: The Grignard reagent prepared in 300 ml of THF from 24 g (1.0 mole) of magnesium and 42 g (0.30 mole) of β-bromostyrene is decanted from excess metal and added dropwise under nitrogen to a solution of 27 g (0.21 moles) of N-methyl glutarimide at 3°- 5°. After 11/2 hrs. at room temperature, the mixture is treated with 250 ml of saturated NH4Cl solution with cooling. The separated aqueous layer is reextracted and the combined THF extracts washed with salt, dried over MgSO4 and freed of solvent. Product is extracted into hot ether and crystallized on cooling to yield white crystals, mp 108°- 112° C. is decanted from excess metal 2 hrs with cooling the combined THF extracts washed with salt dried over MgSO4 Product is extracted into hot ether crystallized on cooling to yield white crystals, mp 108°- 112° C.

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

Procedure: The Grignard reagent prepared in 300 ml of THF from 24 g (1.0 mole) of magnesium and 42 g (0.30 mole) of β-bromostyrene is decanted from excess metal and added dropwise under nitrogen to a solution of 27 g (0.21 moles) of N-methyl glutarimide at 3°- 5°. After 11/2 hrs. at room temperature, the mixture is treated with 250 ml of saturated NH4Cl solution with cooling. The separated aqueous layer is reextracted and the combined THF extracts washed with salt, dried over MgSO4 and freed of solvent. Product is extracted into hot ether and crystallized on cooling to yield white crystals, mp 108°- 112° C. is decanted from excess metal 2 hrs with cooling the combined THF extracts washed with salt dried over MgSO4 Product is extracted into hot ether crystallized on cooling to yield white crystals, mp 108°- 112° C.

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a nitrogen atmosphere, a mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.50 g), β-bromostyrene (1.45 g), bis(triphenylphosphine)palladium(II) dichloride (506 mg), potassium carbonate (1.30 g), ethanol (3.8 mL) and dimethylformamide (7.5 mL) was stirred at 75° C. for 6 hours. Thereafter, 13-bromostyrene (1.45 g) was further added to the reaction solution, and the obtained solution was then stirred at 75° C. for 4 hours. Subsequently, the reaction solution was diluted with ethyl acetate, and was then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=4:1 to 3:1), so as to obtain the title compound (990 mg) in the form of a light yellow solid. the obtained solution was then stirred at 75° C. for 4 hours was then washed with water The organic layer was dried over anhydrous magnesium sulfate was then concentrated under a reduced pressure The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=4:1 to 3:1)

Conditions: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Proceeding as in Example 1, into a 100 cc flask were placed to react: 4.1 g of potassium 3-butenoate (3.3 10-2 mols), 6 g of styryl bromide, a cis-trans mixture, (3.3 10-2 mols), 2.9 g of Ni(PPh3)3 (3.3 10-2 mols) and 40 cc of ethyl alcohol. The mass was heated up to 105° C. under nitrogen atmosphere, for about 2 hours. Operating as in Example 1, there were obtained 2.2 g of 6-phenyl-3,5-hexadienoic acid, a mixture of isomers containing double cis and trans bonds. Proceeding as in Example 1, into a 100 cc flask were placed to react

Conditions: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Proceeding as in Example 1, into a 100 cc flask were placed to react: 4.1 g of potassium 3-butenoate (3.3 10-2 mols), 6 g of styryl bromide, a cis-trans mixture, (3.3 10-2 mols), 2.9 g of Ni(PPh3)3 (3.3 10-2 mols) and 40 cc of ethyl alcohol. The mass was heated up to 105° C. under nitrogen atmosphere, for about 2 hours. Operating as in Example 1, there were obtained 2.2 g of 6-phenyl-3,5-hexadienoic acid, a mixture of isomers containing double cis and trans bonds. Proceeding as in Example 1, into a 100 cc flask were placed to react

Conditions: temp:2.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a three-neck flask under argon and while being stirred mechanically, 11.7 g (480 mmol) of magnesium chips and some iodine crystals in 40 ml of a solution A (55% diethyl ether, 45% tetrahydrofuran) are mixed together. Then, a solution of 80.0 g (436 mmol) of bromostyrene, dissolved in 210 ml of solvent mixture A, is slowly added in drops, and thus a continuous exothermic reaction is achieved. The solution is stirred under reflux. After the end of the exothermic reaction, the reaction mixture is cooled to 2° C., and then 155.5 g (872 mmol) of methyltriethoxysilane in 160 ml of dry diethyl ether is added; the temperature must not exceed 15° C. After the end of the substitution reaction, stirring is continued at room temperature overnight. Approximately 200 ml of n-heptane is then added, thus the magnesium salts precipitate. The latter are filtered off, 9.7·10−2 g (0.44 mmol) of 2,5-di-tert-butylhydroquinone is added to the filtrate, the solvent is drawn off in a rotary evaporator, and the residue is distilled in fractionated form under vacuum. 72.5 g (307 mmol) of the product was obtained with a yield: 70.3%, and a boiling point of 65-66° C. (0.05 mbar) is slowly added in drops thus a continuous exothermic reaction The solution is stirred under reflux After the end of the exothermic reaction exceed 15° C After the end of the substitution reaction stirring thus the magnesium salts precipitate The latter are filtered off the solvent is drawn off in a rotary evaporator the residue is distilled in fractionated form under vacuum

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

Procedure: The Grignard reagent prepared in 300 ml of THF from 24 g (1.0 mole) of magnesium and 42 g (0.30 mole) of β-bromostyrene is decanted from excess metal and added dropwise under nitrogen to a solution of 27 g (0.21 moles) of N-methyl glutarimide at 3°- 5°. After 11/2 hrs. at room temperature, the mixture is treated with 250 ml of saturated NH4Cl solution with cooling. The separated aqueous layer is reextracted and the combined THF extracts washed with salt, dried over MgSO4 and freed of solvent. Product is extracted into hot ether and crystallized on cooling to yield white crystals, mp 108°- 112° C. is decanted from excess metal 2 hrs with cooling the combined THF extracts washed with salt dried over MgSO4 Product is extracted into hot ether crystallized on cooling to yield white crystals, mp 108°- 112° C.

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a nitrogen atmosphere, a mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.50 g), β-bromostyrene (1.45 g), bis(triphenylphosphine)palladium(II) dichloride (506 mg), potassium carbonate (1.30 g), ethanol (3.8 mL) and dimethylformamide (7.5 mL) was stirred at 75° C. for 6 hours. Thereafter, 13-bromostyrene (1.45 g) was further added to the reaction solution, and the obtained solution was then stirred at 75° C. for 4 hours. Subsequently, the reaction solution was diluted with ethyl acetate, and was then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=4:1 to 3:1), so as to obtain the title compound (990 mg) in the form of a light yellow solid. the obtained solution was then stirred at 75° C. for 4 hours was then washed with water The organic layer was dried over anhydrous magnesium sulfate was then concentrated under a reduced pressure The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=4:1 to 3:1)

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

Conditions: temp:2.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a three-neck flask under argon and while being stirred mechanically, 11.7 g (480 mmol) of magnesium chips and some iodine crystals in 40 ml of a solution A (55% diethyl ether, 45% tetrahydrofuran) are mixed together. Then, a solution of 80.0 g (436 mmol) of bromostyrene, dissolved in 210 ml of solvent mixture A, is slowly added in drops, and thus a continuous exothermic reaction is achieved. The solution is stirred under reflux. After the end of the exothermic reaction, the reaction mixture is cooled to 2° C., and then 155.5 g (872 mmol) of methyltriethoxysilane in 160 ml of dry diethyl ether is added; the temperature must not exceed 15° C. After the end of the substitution reaction, stirring is continued at room temperature overnight. Approximately 200 ml of n-heptane is then added, thus the magnesium salts precipitate. The latter are filtered off, 9.7·10−2 g (0.44 mmol) of 2,5-di-tert-butylhydroquinone is added to the filtrate, the solvent is drawn off in a rotary evaporator, and the residue is distilled in fractionated form under vacuum. 72.5 g (307 mmol) of the product was obtained with a yield: 70.3%, and a boiling point of 65-66° C. (0.05 mbar) is slowly added in drops thus a continuous exothermic reaction The solution is stirred under reflux After the end of the exothermic reaction exceed 15° C After the end of the substitution reaction stirring thus the magnesium salts precipitate The latter are filtered off the solvent is drawn off in a rotary evaporator the residue is distilled in fractionated form under vacuum

Conditions: temp:2.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a three-neck flask under argon and while being stirred mechanically, 11.7 g (480 mmol) of magnesium chips and some iodine crystals in 40 ml of a solution A (55% diethyl ether, 45% tetrahydrofuran) are mixed together. Then, a solution of 80.0 g (436 mmol) of bromostyrene, dissolved in 210 ml of solvent mixture A, is slowly added in drops, and thus a continuous exothermic reaction is achieved. The solution is stirred under reflux. After the end of the exothermic reaction, the reaction mixture is cooled to 2° C., and then 155.5 g (872 mmol) of methyltriethoxysilane in 160 ml of dry diethyl ether is added; the temperature must not exceed 15° C. After the end of the substitution reaction, stirring is continued at room temperature overnight. Approximately 200 ml of n-heptane is then added, thus the magnesium salts precipitate. The latter are filtered off, 9.7·10−2 g (0.44 mmol) of 2,5-di-tert-butylhydroquinone is added to the filtrate, the solvent is drawn off in a rotary evaporator, and the residue is distilled in fractionated form under vacuum. 72.5 g (307 mmol) of the product was obtained with a yield: 70.3%, and a boiling point of 65-66° C. (0.05 mbar) is slowly added in drops thus a continuous exothermic reaction The solution is stirred under reflux After the end of the exothermic reaction exceed 15° C After the end of the substitution reaction stirring thus the magnesium salts precipitate The latter are filtered off the solvent is drawn off in a rotary evaporator the residue is distilled in fractionated form under vacuum