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

HRID 1631497Notes

Reaction equation

HRID 1631497 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-2d7befa0ded045eebfb4165cd67ff2b8
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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