Water → 2-(4-Bromophenyl)-4-methoxy-2H-1,2,3-triazole

HRID 468644Notes

Reaction equation

HRID 468644 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[N:18]=[C:17](O)[CH:16]=[N:15]2)=[CH:10][CH:9]=1.CI.O>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[N:18]=[C:17]([O:4][CH3:1])[CH:16]=[N:15]2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178516800HCID 178516800, compound

Product 1

HCID 672492502-(4-Bromophenyl)-4-methoxy-2H-1,2,3-triazoleYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Cesium carbonate (4.5 g, 13.7 mmol) was added to a solution of 2-(4-bromophenyl)-2H-1,2,3-triazol-4-ol (1.1 g, 4.6 mmol) and methyl iodide (0.36 mL, 5.7 mmol) in THF (50 mL). The reaction was heated to 60° C. and stirred at this temperature for 16 h. Water (20 mL) was added to the reaction, and the resulting mixture was extracted with EtOAc (2×150 mL). The combined organic phases were dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford the title compound as a tan solid (1.1 g, 95%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 3.98 (s, 3H) 7.39 (s, 1H) 7.55-7.62 (m, 2H) 7.79-7.86 (m, 2H).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (2×150 mL)
  2. dry with materialThe combined organic phases were dried over potassium carbonate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfd3199b01284a9caf737e5964968486
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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