Br[CH2:2][C:3]1[C:4]([Cl:11])=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[N-:12]=[N+]=[N-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>CN(C=O)C.CCOC(C)=O>[Cl:11][C:4]1[C:5]([C:6]#[N:7])=[CH:8][CH:9]=[CH:10][C:3]=1[CH2:2][NH2:12]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.
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