Isobutylene → HCID 15411026, compound

HRID 443037Notes

Reaction equation

HRID 443037 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])[N:8]=2)=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.[CH2:31]=[C:32]([CH3:34])[CH3:33]>ClCCl>[C:32]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])[N:8]=2)=[CH:21][CH:22]=1)([CH3:34])([CH3:33])[CH3:31]

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 62406Trifluoromethanesulfonic acidHCID 53742074HCID 53742074, compound

Product 1

HCID 15411026HCID 15411026, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.6 g of 5-(4-hydroxybenzyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole in 10 ml of dichloromethane at -70° C. was added 0.29 g of trifluoromethanesulfonic acid and 2.1 g of isobutene was bubbled in a few minutes. After 1 hour of stirring at the same temperature, triethyamine was added to the solution and then the reaction mixture was warmed gradually to room temperature. The reaction mixture was poured into iced water and the organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 0.55 g of 5-(4-t-butoxybenzyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole. nD22.8 1.5458

Workup

  1. customwas bubbled in a few minutes
  2. additionwas added to the solution
  3. additionThe reaction mixture was poured into iced water
  4. washthe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea6bc59c07854b5cbda63806d588a275
Source dataset
uspto-grants-1999_04
Patent number
US05892048

Reaction notes

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