Water → 4-(Bromomethyl)-5-methyl-2-phenyl-2H-1,2,3-triazole

HRID 415687Notes

Reaction equation

HRID 415687 reaction equation
[CH3:1][C:2]1[C:3]([CH2:13]O)=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.P(Br)(Br)[Br:16].O>C1(C)C=CC=CC=1>[Br:16][CH2:13][C:3]1[C:2]([CH3:1])=[N:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 563195(5-Methyl-2-phenyl-2H-1,2,3-triazol-4-yl)methanol

Product 1

HCID 3387104-(Bromomethyl)-5-methyl-2-phenyl-2H-1,2,3-triazoleYield 91.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (5-Methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-methanol (0.25 g, 1.30 mmol) in 10 ml of toluene was added PBr3 (0.53 g, 1.90 mmol) and the reaction mixture was heated at 120° C. for 20 min under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to get the desired product (0.30 g, 90%) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6a3eb7afc01f49c48f952e8dee446fb1
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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