p-Fluoronitrobenzene → HCID 58128472, compound

HRID 1798824Notes

Reaction equation

HRID 1798824 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[N:3]=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:6]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178434708HCID 178434708, compound

Product 1

HCID 58128472HCID 58128472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-methyl-1H-tetrazole (715 mg, 8.5 mmol) was dissolved in DMF (7 mL) in a 40 mL biotage microwave tube. 4-fluoro-nitrobenzene (1 g, 7.09 mmol) was added, followed by addition of potassium carbonate (1.175 g, 8.5 mmol). The tube was crimp sealed and heated at 110° C. for 4 hours (caution: build-up of pressure possible; use a safety shield). TLC indicated complete consumption of starting materials. Most DMF was removed under vacuum. Water (50 mL) was added. Large amount of brown solid formed (1 gram) and was collected by filtration. The solid was further purified by column through a 80 gram biotage silica gel cartridge using 30-75% ethyl acetate/hexanes to give clean fraction of 5-methyl-2-(4-nitrophenyl)-2H-tetrazole, LRMS calc: 205.1; obs: 206.3 (W+1).

Workup

  1. customThe tube was crimp sealed
  2. customconsumption of starting materials
  3. customMost DMF was removed under vacuum
  4. additionWater (50 mL) was added
  5. customLarge amount of brown solid formed (1 gram)
  6. filtrationwas collected by filtration
  7. customThe solid was further purified by column through a 80 gram biotage silica gel cartridge

Sources & evidence

ORD record
ord-b951f402c3704a6491a39d0a18d934d0
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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