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

HRID 84298Notes

Reaction equation

HRID 84298 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:12]=[C:11]([OH:13])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:14]1COCC1.C(=O)([O-])[O-].[Cs+].[Cs+].CI>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[N:12]=[C:11]([O:13][CH3:14])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 178516800HCID 178516800, compound

Product 1

HCID 672492502-(4-Bromophenyl)-4-methoxy-2H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-(4-bromophenyl)-2H-1,2,3-triazol-4-ol (200 mg, 0.833 mmol) was weighed into a 20 ml vial equipped with a septa cap. THF (10.0 ml) was added. To this was added cesium carbonate (814 mg, 2.5 mmol), followed by the addition of methyl iodide (65.8 uL, 1.04 mmol) via syringe. The reaction was heated at 60° C. for 16 hours. Water (20 ml) was added and the product was extracted with ethyl acetate (2×75 ml). Organic phases were combined, dried over potassium carbonate, filtered and concentrated to furnish a light tan solid (190 mg, 89% TY). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.04 (s, 3 H) 7.30 (s, 1 H) 7.56 (d, J=8.98 Hz, 2 H) 7.84 (d, J=8.98 Hz, 2 H)

Workup

  1. customvial equipped with a septa cap
  2. extractionthe product was extracted with ethyl acetate (2×75 ml)
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto furnish a light tan solid (190 mg, 89% TY)

Sources & evidence

ORD record
ord-d1de72ed4fe9433d8b5c149aaaad6579
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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