1,2-Dibromoethane → 1-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

HRID 474239Notes

Reaction equation

HRID 474239 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=2[OH:16])[N:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:23][CH2:24][CH2:25]Br>CC#N>[Br:23][CH2:24][CH2:25][O:16][C:8]1[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=1[N:4]1[CH:5]=[N:6][C:2]([CH3:1])=[N:3]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 666682322-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenol

Product 1

HCID 666688591-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazoleYield 49.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenol (3 g, 13.63 mmol) and K2CO3 (2.4 g, 17.79 mmol) in MeCN (30 mL) was added 1,2-dibromoethane (3.3 g, 17.71 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL) and washed with brine (2×25 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to give 1-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (2.2 g, 49.5%) as a light orange solid. LC-MS (M+H)+=327.13. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.15 (1H, s), 8.09-8.04 (3H, m), 4.70-4.69 (2H, m), 3.99-3.97 (2H, m), 2.40 (3H, s).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with brine (2×25 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32ac3c16eae64da79efbd391fc1698bb
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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