Phosphorus tribromide → 5-(Bromomethyl)-1-methyl-1H-benzotriazole

Reaction equation

P(Br)(Br)[Br:2].[CH3:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15]O)=[CH:14][C:9]=2[N:8]=[N:7]1>C(OCC)C.O>[Br:2][CH2:15][C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH3:5])[N:7]=[N:8][C:9]=2[CH:14]=1

Participants

Procedure

Phosphorus tribromide (0.230 ml, 2.45 mmol) is added to a stirred solution of (1-methyl-1H-1,2,3-benzotriazole-5-yl)methanol (0.4 g, 2.45 mmol) in diethyl ether (25 ml) under an inert atmosphere of Argon. After stirring overnight at room temperature, the reaction mixture is diluted with water (5 ml) and stirred vigorously for 10 minutes. The organic portion is separated, washed with water (2×5 ml), brine (2×5 ml) and concentrated in vacuo to yield the titled product which is used crude in the next step. (MH+226).