3-(Bromomethyl)-2-chlorobenzonitrile

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a soln. of 3-(bromomethyl)-2-chlorobenzonitrile (0.87 mmol) in 9 mL DMF was added NaN3 (1.3 mmol) and the resulting brown solution was stirred at RT for 20 min. The reaction mixture was diluted with EtOAc, washed twice with water and brine, dried over MgSO4 and concentrated in vacuo. The crude azide was redissolved in 4.3 mL THF and 0.1 mL water. Triphenylphosphine (1.04 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was acidified with 0.1; N HCl soln. until pH 3 and it was extracted 3 times with Et2O. The aq. phase was basified with 1M NaOH soln. and extracted 3 times with DCM. The comb. org. layers were dried over MgSO4 and conc. in vacuo to give the desired product as yellowish oil. washed twice with water and brine dried over MgSO4 concentrated in vacuo The crude azide was redissolved in 4.3 mL THF the mixture was stirred at RT overnight until pH 3 and it was extracted 3 times with Et2O and extracted 3 times with DCM layers were dried over MgSO4 and conc. in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a soln. of 3-(bromomethyl)-2-chlorobenzonitrile (0.87 mmol) in 9 mL DMF was added NaN3 (1.3 mmol) and the resulting brown solution was stirred at RT for 20 min. The reaction mixture was diluted with EtOAc, washed twice with water and brine, dried over MgSO4 and concentrated in vacuo. The crude azide was redissolved in 4.3 mL THF and 0.1 mL water. Triphenylphosphine (1.04 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was acidified with 0.1; N HCl soln. until pH 3 and it was extracted 3 times with Et2O. The aq. phase was basified with 1M NaOH soln. and extracted 3 times with DCM. The comb. org. layers were dried over MgSO4 and conc. in vacuo to give the desired product as yellowish oil. washed twice with water and brine dried over MgSO4 concentrated in vacuo The crude azide was redissolved in 4.3 mL THF the mixture was stirred at RT overnight until pH 3 and it was extracted 3 times with Et2O and extracted 3 times with DCM layers were dried over MgSO4 and conc. in vacuo

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A soln. of 2-chloro-3-methylbenzonitrile (6.6 mmol) in 25 mL chlorobenzene was heated to 50° C. when NBS (7.9 mmol) was added. The flask was purged with Ar before AIBN (0.66 mmol) was added at once still at 50° C. The reaction mixture was stirred at 80° C. for 2 h. The solvent was evaporated off, the resulting residue was redissolved in Et2O and washed 3 times with 1N HCl soln. and brine. It was dried over MgSO4 and conc. in vacuo. Purification with CC (0-15% EtOAc/Hept) gives the desired compound as white solid. was added was added at once still at 50° C The solvent was evaporated off the resulting residue was redissolved in Et2O washed 3 times with 1N HCl soln It was dried over MgSO4 and conc. in vacuo Purification with CC (0-15% EtOAc/Hept)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-(bromomethyl)-2-chlorobenzonitrile (0.87 mmol) in 9 mL DMF was added NaN3 (1.3 mmol) and the resulting brown solution was stirred at RT for 20 min. The reaction mixture was diluted with EtOAc, washed twice with water and brine, dried over MgSO4 and concentrated in vacuo. The crude azide was redissolved in 4.3 mL THF and 0.1 mL water. Triphenylphosphine (1.04 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was acidified with 0.1N HCl solution until pH 3 and it was extracted 3 times with Et2O. The ageous phase was basified with 1M NaOH solution and extracted 3 times with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as yellowish oil. washed twice with water and brine dried over MgSO4 concentrated in vacuo The crude azide was redissolved in 4.3 mL THF the mixture was stirred at RT overnight was extracted 3 times with Et2O extracted 3 times with DCM The combined organic layers were dried over MgSO4 concentrated in vacuo

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-chloro-3-methylbenzonitrile (6.6 mmol) in 25 mL chlorobenzene was heated to 50° C. when NBS (7.9 mmol) was added. The flask was purged with Ar before AIBN (0.66 mmol) was added at once still at 50° C. The reaction mixture was stirred at 80° C. for 2 h. The solvent was evaporated off, the resulting residue was redissolved in Et2O and washed 3 times with 1N HCl solution and brine. It was dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept to Hept/EtOAc (85/15) gives the desired compound as white solid. was added was added at once still at 50° C The solvent was evaporated off the resulting residue was redissolved in Et2O washed 3 times with 1N HCl solution and brine It was dried over MgSO4 concentrated in vacuo Purification with CC (KP-SIL™ from Biotage)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a soln. of 3-(bromomethyl)-2-chlorobenzonitrile (0.87 mmol) in 9 mL DMF was added NaN3 (1.3 mmol) and the resulting brown solution was stirred at RT for 20 min. The reaction mixture was diluted with EtOAc, washed twice with water and brine, dried over MgSO4 and concentrated in vacuo. The crude azide was redissolved in 4.3 mL THF and 0.1 mL water. Triphenylphosphine (1.04 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was acidified with 0.1; N HCl soln. until pH 3 and it was extracted 3 times with Et2O. The aq. phase was basified with 1M NaOH soln. and extracted 3 times with DCM. The comb. org. layers were dried over MgSO4 and conc. in vacuo to give the desired product as yellowish oil. washed twice with water and brine dried over MgSO4 concentrated in vacuo The crude azide was redissolved in 4.3 mL THF the mixture was stirred at RT overnight until pH 3 and it was extracted 3 times with Et2O and extracted 3 times with DCM layers were dried over MgSO4 and conc. in vacuo

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A soln. of 2-chloro-3-methylbenzonitrile (6.6 mmol) in 25 mL chlorobenzene was heated to 50° C. when NBS (7.9 mmol) was added. The flask was purged with Ar before AIBN (0.66 mmol) was added at once still at 50° C. The reaction mixture was stirred at 80° C. for 2 h. The solvent was evaporated off, the resulting residue was redissolved in Et2O and washed 3 times with 1N HCl soln. and brine. It was dried over MgSO4 and conc. in vacuo. Purification with CC (0-15% EtOAc/Hept) gives the desired compound as white solid. was added was added at once still at 50° C The solvent was evaporated off the resulting residue was redissolved in Et2O washed 3 times with 1N HCl soln It was dried over MgSO4 and conc. in vacuo Purification with CC (0-15% EtOAc/Hept)