Hydrogen Bromide → 1-(4-Hydroxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one

HRID 1182184Notes

Reaction equation

HRID 1182184 reaction equation
CS(O)(=O)=O.C[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:23])[CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1.Br.[OH-].[Na+]>O>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:23])[CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 866078301-(4-Methoxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one methanesulfonate

Product 1

HCID 587108001-(4-Hydroxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.70 g (5.0 mmol) 1-(4-Methoxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one methane-sulfonate and 7 ml 47% aqueous HBr were heated to 80° C. overnight. After diluting with 10 ml water and cooling to 0° C. the mixture was alkalized (pH 12.6) by dropwise addition of 4N NaOH and extracted three times with toluene. Concentration of the toluene phase in vacuo gave 0.05 g recovered starting material. The aqueous phase was cooled and adjusted to pH=6.3 by addition of 6 N HCl. The resulting precipitate was isolated and dried in vacuo at 40° C. to give 1-(4-hydroxy-phenyl)-4-[1,2,3]triazol-1-yl-butan-1-one. Yield: 0.96 g (83%).

Workup

  1. extractionextracted three times with toluene
  2. customConcentration of the toluene phase in vacuo gave 0.05 g
  3. customrecovered
  4. temperatureThe aqueous phase was cooled
  5. additionadjusted to pH=6.3 by addition of 6 N HCl
  6. customThe resulting precipitate was isolated
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-6199f6e7737f450ba944cff9434bff05
Source dataset
uspto-grants-2007_10
Patent number
US07288557B2

Reaction notes

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