(2-benzylphenyl)methanol

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

Procedure: 2-Benzylbenzyl alcohol (commercial) (1 g) was suspended in 48% aqueous hydrobromic acid (10 ml) and stirred vigorously for 20 hours. The resultant suspended solid was extracted twice with hexane and the extracts dried (MgSO4) and evaporated to give 2-benzyl benzylbromide as yellow solid (1.3 g, 98%). was extracted twice with hexane the extracts dried (MgSO4) evaporated

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

Procedure: 2-Benzylbenzyl alcohol (commercial) (1 g) was suspended in 48% aqueous hydrobromic acid (10 ml) and stirred vigorously for 20 hours. The resultant suspended solid was extracted twice with hexane and the extracts dried (MgSO4) and evaporated to give 2-benzyl benzylbromide as yellow solid (1.3 g, 98%). was extracted twice with hexane the extracts dried (MgSO4) evaporated

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

Procedure: 2-Benzylbenzyl alcohol (commercial) (1 g) was suspended in 48% aqueous hydrobromic acid (10 ml) and stirred vigorously for 20 hours. The resultant suspended solid was extracted twice with hexane and the extracts dried (MgSO4) and evaporated to give 2-benzyl benzylbromide as yellow solid (1.3 g, 98%). was extracted twice with hexane the extracts dried (MgSO4) evaporated

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

Procedure: A solution of phosphorus tribromide (2.1 mL, 6.0 g, 22.1 mM) in 30 mL of carbon tetrachloride was slowly added dropwise to solution of 2-benzylbenzyl alcohol (1.98 g, 10 mM) in 70 mL of carbon tetrachloride at 0° C. The mixture was stirred at 0° C. for 2 hours, then at room temperature for 2 hours. The solvent was removed in vacuo and the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 2.6 g (99%) of 2-benzylbenzyl bromide as a yellow solid. 1H NMR (DMSO-d6) δ 7.5-7.0 (m, 9H), 4.7 (s, 2H), and 4.15 (s, 2H). IR (CHCl3, cm−1) 3065, 1601, 1495, and 1453. MS (FD) m/e 260, 262. at room temperature for 2 hours The solvent was removed in vacuo the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate The organic layer was washed with brine dried over magnesium sulfate filtered concentrated

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

Procedure: 2-Benzylbenzyl alcohol (commercial) (1 g) was suspended in 48% aqueous hydrobromic acid (10 ml) and stirred vigorously for 20 hours. The resultant suspended solid was extracted twice with hexane and the extracts dried (MgSO4) and evaporated to give 2-benzyl benzylbromide as yellow solid (1.3 g, 98%). was extracted twice with hexane the extracts dried (MgSO4) evaporated

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

Procedure: A solution of phosphorus tribromide (2.1 mL, 6.0 g, 22.1 mM) in 30 mL of carbon tetrachloride was slowly added dropwise to solution of 2-benzylbenzyl alcohol (1.98 g, 10 mM) in 70 mL of carbon tetrachloride at 0° C. The mixture was stirred at 0° C. for 2 hours, then at room temperature for 2 hours. The solvent was removed in vacuo and the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 2.6 g (99%) of 2-benzylbenzyl bromide as a yellow solid. 1H NMR (DMSO-d6) δ7.5-7.0 (m, 9H), 4.7 (s, 2H), and 4.15 (s, 2H). IR (CDCl3, cm−1) 3065, 1601, 1495, and 1453. MS (FD) m/e 260, 262. at room temperature for 2 hours The solvent was removed in vacuo the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate The organic layer was washed with brine dried over magnesium sulfate filtered concentrated

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

Procedure: A solution of phosphorus tribromide (2.1 mL, 6.0 g, 22.1 mM) in 30 mL of carbon tetrachloride was slowly added dropwise to solution of 2-benzylbenzyl alcohol (1.98 g, 10 mM) in 70 mL of carbon tetrachloride at 0° C. The mixture was stirred at 0° C. for 2 hours, then at room temperature for 2 hours. The solvent was removed in vacuo and the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 2.6 g (99%) of 2-benzylbenzyl bromide as a yellow solid. 1H NMR (DMSO-d6) δ7.5-7.0 (m, 9H), 4.7 (s, 2H), and 4.15 (s, 2H). IR (CDCl3, cm−1) 3065, 1601, 1495, and 1453. MS (FD) m/e 260, 262. at room temperature for 2 hours The solvent was removed in vacuo the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate The organic layer was washed with brine dried over magnesium sulfate filtered concentrated

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

Procedure: Sodium hydride (2.1 g, 53 mmol, 60% oil dispersion) was added portionwise to a stirred solution of 2-benzylbenzylalcohol (5.0 g, 25 mmol) in dry THF (125 ml) placed under an atmosphere of nitrogen. The mixture was heated at reflux for 1 h and then allowed to cool to ambient temperature within 30 minutes. (R)-1-(2-Bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (8.6 g, 25 mmol, EP 374801) was added and the mixture was stirred for 2 days at ambient temperature. The reaction mixture was diluted with THF (100 ml) and filtered. The solvent was evaporated in vacuo to give an oily residue which was purified by column chromatography (700 g, heptane/ethyl acetate=1/1) to give 0.8 g of (R)-1-(2-(2-benzylbenzyloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil. The mixture was heated at reflux for 1 h filtered The solvent was evaporated in vacuo to give an oily residue which was purified by column chromatography (700 g, heptane/ethyl acetate=1/1)

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

Procedure: 2-Benzylbenzyl alcohol (commercial) (1 g) was suspended in 48% aqueous hydrobromic acid (10 ml) and stirred vigorously for 20 hours. The resultant suspended solid was extracted twice with hexane and the extracts dried (MgSO4) and evaporated to give 2-benzyl benzylbromide as yellow solid (1.3 g, 98%). was extracted twice with hexane the extracts dried (MgSO4) evaporated

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

Procedure: 2-Benzylbenzyl alcohol (commercial) (1 g) was suspended in 48% aqueous hydrobromic acid (10 ml) and stirred vigorously for 20 hours. The resultant suspended solid was extracted twice with hexane and the extracts dried (MgSO4) and evaporated to give 2-benzyl benzylbromide as yellow solid (1.3 g, 98%). was extracted twice with hexane the extracts dried (MgSO4) evaporated

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

Procedure: A solution of phosphorus tribromide (2.1 mL, 6.0 g, 22.1 mM) in 30 mL of carbon tetrachloride was slowly added dropwise to solution of 2-benzylbenzyl alcohol (1.98 g, 10 mM) in 70 mL of carbon tetrachloride at 0° C. The mixture was stirred at 0° C. for 2 hours, then at room temperature for 2 hours. The solvent was removed in vacuo and the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 2.6 g (99%) of 2-benzylbenzyl bromide as a yellow solid. 1H NMR (DMSO-d6) δ 7.5-7.0 (m, 9H), 4.7 (s, 2H), and 4.15 (s, 2H). IR (CHCl3, cm−1) 3065, 1601, 1495, and 1453. MS (FD) m/e 260, 262. at room temperature for 2 hours The solvent was removed in vacuo the residue diluted with ethyl acetate and saturated aqueous sodium bicarbonate The organic layer was washed with brine dried over magnesium sulfate filtered concentrated

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

Procedure: 2-Benzylbenzyl alcohol (commercial) (1 g) was suspended in 48% aqueous hydrobromic acid (10 ml) and stirred vigorously for 20 hours. The resultant suspended solid was extracted twice with hexane and the extracts dried (MgSO4) and evaporated to give 2-benzyl benzylbromide as yellow solid (1.3 g, 98%). was extracted twice with hexane the extracts dried (MgSO4) evaporated