Tetrabutylammonium Fluoride → HCID 20373983, compound

HRID 2190313Notes

Reaction equation

HRID 2190313 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([Si](C)(C)C)[N:10]=[N:9]2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOC(C)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57586422HCID 57586422, compound

Product 1

HCID 20373983HCID 20373983, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 1-(4-iodophenyl)-4-(trimethylsilyl)-1H-1,2,3-triazole, prepared in the previous step, at room temperature was added tetrabutylammonium fluoride (1 M in THF, 50 mL, 50 mmol). The reaction mixture was heated to 50° C. for 1.5 h and diluted with EtOAc. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in hexanes) gave 1-(4-iodophenyl)-1H-1,2,3-triazole.

Workup

  1. washThe organic phase was washed with water (2×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bcca977000b94936aa04ae2a2c5e38e9
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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