(4-Vinylphenyl)methanol

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

Procedure: A DMF suspension (5 ml) of sodium hydride (50% in oil, 240 mg, 5.0 mmoles) was cooled to 0° C. under an argon atmosphere, and a DMF (1 ml) solution of 1.34 g of 4-vinylbenzyl alcohol (10 mmoles) was added. The reaction mixture was agitated for fifteen minutes, and a DMF solution (3 ml) of 3.66 g of 1,6-dibromohexane (15 mmoles) was added over at least five minutes. The reaction mixture was agitated at room temperature for three hours. Fifteen milliliters of water was added to the reaction solution while cooling using ice, and the solution was agitated for five minutes. The solution was extracted using ethyl acetate (2×40 ml). The combined organic layers were washed using 15 ml of saturated aqueous saline solution and dried using anhydrous sodium sulfate. Upon filtration and concentration, 4.11 g of the residue was purified using silica gel column chromatography (70 g silica gel, 20:1 hexane/Et2O) and 1.72 g of 6-(4-vinylbenzyloxy)bromohexane (5.8 mmoles, 58%) was obtained in the form of an oily substance. The reaction mixture was agitated at room temperature for three hours while cooling the solution was agitated for five minutes The solution was extracted The combined organic layers were washed dried Upon filtration and concentration, 4.11 g of the residue was purified

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32–7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

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

Procedure: A DMF suspension (5 ml) of sodium hydride (50% in oil, 240 mg, 5.0 mmoles) was cooled to 0° C. under an argon atmosphere, and a DMF (1 ml) solution of 1.34 g of 4-vinylbenzyl alcohol (10 mmoles) was added. The reaction mixture was agitated for fifteen minutes, and a DMF solution (3 ml) of 3.66 g of 1,6-dibromohexane (15 mmoles) was added over at least five minutes. The reaction mixture was agitated at room temperature for three hours. Fifteen milliliters of water was added to the reaction solution while cooling using ice, and the solution was agitated for five minutes. The solution was extracted using ethyl acetate (2×40 ml). The combined organic layers were washed using 15 ml of saturated aqueous saline solution and dried using anhydrous sodium sulfate. Upon filtration and concentration, 4.11 g of the residue was purified using silica gel column chromatography (70 g silica gel, 20:1 hexane/Et2O) and 1.72 g of 6-(4-vinylbenzyloxy)bromohexane (5.8 mmoles, 58%) was obtained in the form of an oily substance. The reaction mixture was agitated at room temperature for three hours while cooling the solution was agitated for five minutes The solution was extracted The combined organic layers were washed dried Upon filtration and concentration, 4.11 g of the residue was purified

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

Procedure: A DMF suspension (5 ml) of sodium hydride (50% in oil, 240 mg, 5.0 mmoles) was cooled to 0° C. under an argon atmosphere, and a DMF (1 ml) solution of 1.34 g of 4-vinylbenzyl alcohol (10 mmoles) was added. The reaction mixture was agitated for fifteen minutes, and a DMF solution (3 ml) of 3.66 g of 1,6-dibromohexane (15 mmoles) was added over at least five minutes. The reaction mixture was agitated at room temperature for three hours. Fifteen milliliters of water was added to the reaction solution while cooling using ice, and the solution was agitated for five minutes. The solution was extracted using ethyl acetate (2×40 ml). The combined organic layers were washed using 15 ml of saturated aqueous saline solution and dried using anhydrous sodium sulfate. Upon filtration and concentration, 4.11 g of the residue was purified using silica gel column chromatography (70 g silica gel, 20:1 hexane/Et2O) and 1.72 g of 6-(4-vinylbenzyloxy)bromohexane (5.8 mmoles, 58%) was obtained in the form of an oily substance. The reaction mixture was agitated at room temperature for three hours while cooling the solution was agitated for five minutes The solution was extracted The combined organic layers were washed dried Upon filtration and concentration, 4.11 g of the residue was purified

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32–7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H). The reaction mixture was washed with water (1×) The organic solution was dried over MgSO4 filtered concentrated in vacuo The product was triturated with petroleum ether (3×) the ethereal solution was concentrated in vacuo The residue was purified by flash chromatography (hexanes)

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

Procedure: A DMF suspension (5 ml) of sodium hydride (50% in oil, 240 mg, 5.0 mmoles) was cooled to 0° C. under an argon atmosphere, and a DMF (1 ml) solution of 1.34 g of 4-vinylbenzyl alcohol (10 mmoles) was added. The reaction mixture was agitated for fifteen minutes, and a DMF solution (3 ml) of 3.66 g of 1,6-dibromohexane (15 mmoles) was added over at least five minutes. The reaction mixture was agitated at room temperature for three hours. Fifteen milliliters of water was added to the reaction solution while cooling using ice, and the solution was agitated for five minutes. The solution was extracted using ethyl acetate (2×40 ml). The combined organic layers were washed using 15 ml of saturated aqueous saline solution and dried using anhydrous sodium sulfate. Upon filtration and concentration, 4.11 g of the residue was purified using silica gel column chromatography (70 g silica gel, 20:1 hexane/Et2O) and 1.72 g of 6-(4-vinylbenzyloxy)bromohexane (5.8 mmoles, 58%) was obtained in the form of an oily substance. The reaction mixture was agitated at room temperature for three hours while cooling the solution was agitated for five minutes The solution was extracted The combined organic layers were washed dried Upon filtration and concentration, 4.11 g of the residue was purified