2-[(4-bromophenyl)iminomethyl]phenol

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

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

Procedure: A 60% dispersion of sodium hydride in mineral oil (0.145 g, 0.00362 mol) was added to a solution of trimethylsulfoxonium iodide (0.8 g, 0.00362 mol) in anhydrous dimethylsulfoxide (10 mL) and the resulting mixture was stirred under an atmosphere of nitrogen for 10 min. A solution of 2-{[(4-bromophenyl)imino]methyl}phenol (0.4 g, 0.00145 mol) in anhydrous dimethylsulfoxide (5 mL) was added dropwise and the resulting mixture was stirred at ambient temperature for 2.5 hours. It was poured into ice-cold water (100 mL) and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure to yield N-(4-bromophenyl)-N-(2,3-dihydrobenzo[b]furan-3-yl)amine (0.321 g, 0.0011 mol) as an off-white solid. the resulting mixture was stirred at ambient temperature for 2.5 hours extracted with diethyl ether (2×50 mL) The combined organic extracts were dried with magnesium sulfate concentrated under reduced pressure

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

Procedure: A 60% dispersion of sodium hydride in mineral oil (0.145 g, 0.00362 mol) was added to a solution of trimethylsulfoxonium iodide (0.8 g, 0.00362 mol) in anhydrous dimethylsulfoxide (10 mL) and the resulting mixture was stirred under an atmosphere of nitrogen for 10 min. A solution of 2-{[(4-bromophenyl)imino]methyl}phenol (0.4 g, 0.00145 mol) in anhydrous dimethylsulfoxide (5 mL) was added dropwise and the resulting mixture was stirred at ambient temperature for 2.5 hours. It was poured into ice-cold water (100 mL) and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure to yield N-(4-bromophenyl)-N-(2,3-dihydrobenzo[b]furan-3-yl)amine (0.321 g, 0.0011 mol) as an off-white solid. the resulting mixture was stirred at ambient temperature for 2.5 hours extracted with diethyl ether (2×50 mL) The combined organic extracts were dried with magnesium sulfate concentrated under reduced pressure

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

Procedure: A 60% dispersion of sodium hydride in mineral oil (0.145 g, 0.00362 mol) was added to a solution of trimethylsulfoxonium iodide (0.8 g, 0.00362 mol) in anhydrous dimethylsulfoxide (10 mL) and the resulting mixture was stirred under an atmosphere of nitrogen for 10 min. A solution of 2-{[(4-bromophenyl)imino]methyl}phenol (0.4 g, 0.00145 mol) in anhydrous dimethylsulfoxide (5 mL) was added dropwise and the resulting mixture was stirred at ambient temperature for 2.5 hours. It was poured into ice-cold water (100 mL) and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure to yield N-(4-bromophenyl)-N-(2,3-dihydrobenzo[b]furan-3-yl)amine (0.321 g, 0.0011 mol) as an off-white solid. the resulting mixture was stirred at ambient temperature for 2.5 hours extracted with diethyl ether (2×50 mL) The combined organic extracts were dried with magnesium sulfate concentrated under reduced pressure

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

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

Procedure: A 60% dispersion of sodium hydride in mineral oil (0.145 g, 0.00362 mol) was added to a solution of trimethylsulfoxonium iodide (0.8 g, 0.00362 mol) in anhydrous dimethylsulfoxide (10 mL) and the resulting mixture was stirred under an atmosphere of nitrogen for 10 min. A solution of 2-{[(4-bromophenyl)imino]methyl}phenol (0.4 g, 0.00145 mol) in anhydrous dimethylsulfoxide (5 mL) was added dropwise and the resulting mixture was stirred at ambient temperature for 2.5 hours. It was poured into ice-cold water (100 mL) and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure to yield N-(4-bromophenyl)-N-(2,3-dihydrobenzo[b]furan-3-yl)amine (0.321 g, 0.0011 mol) as an off-white solid. the resulting mixture was stirred at ambient temperature for 2.5 hours extracted with diethyl ether (2×50 mL) The combined organic extracts were dried with magnesium sulfate concentrated under reduced pressure

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

Procedure: A 60% dispersion of sodium hydride in mineral oil (0.145 g, 0.00362 mol) was added to a solution of trimethylsulfoxonium iodide (0.8 g, 0.00362 mol) in anhydrous dimethylsulfoxide (10 mL) and the resulting mixture was stirred under an atmosphere of nitrogen for 10 min. A solution of 2-{[(4-bromophenyl)imino]methyl}phenol (0.4 g, 0.00145 mol) in anhydrous dimethylsulfoxide (5 mL) was added dropwise and the resulting mixture was stirred at ambient temperature for 2.5 hours. It was poured into ice-cold water (100 mL) and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure to yield N-(4-bromophenyl)-N-(2,3-dihydrobenzo[b]furan-3-yl)amine (0.321 g, 0.0011 mol) as an off-white solid. the resulting mixture was stirred at ambient temperature for 2.5 hours extracted with diethyl ether (2×50 mL) The combined organic extracts were dried with magnesium sulfate concentrated under reduced pressure