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

HRID 1754499Notes

Reaction equation

HRID 1754499 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

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 2776552(1-Methyl-1H-benzotriazol-5-yl)methanol

Product 1

HCID 27954185-(Bromomethyl)-1-methyl-1H-benzotriazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

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).

Workup

  1. stirringstirred vigorously for 10 minutes
  2. customThe organic portion is separated
  3. washwashed with water (2×5 ml), brine (2×5 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be6a705bdd954863b4fff2d7bd9691a7
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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