Water → HCID 18787018, compound

HRID 1107298Notes

Reaction equation

HRID 1107298 reaction equation
[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:21]=[C:22]([C:31]2[N:32]=[N:33][NH:34][CH:35]=2)[CH:23]=[CH:24][C:25]=1[O:26][C:27]([F:30])([F:29])[F:28].S(OC)(O[CH3:40])(=O)=O.O>C1COCC1.C(OCC)C>[CH3:2][N:33]1[N:32]=[C:31]([C:22]2[CH:23]=[CH:24][C:25]([O:26][C:27]([F:28])([F:29])[F:30])=[C:20]([Br:19])[CH:21]=2)[CH:35]=[N:34]1.[CH3:40][N:34]1[CH:35]=[C:31]([C:22]2[CH:23]=[CH:24][C:25]([O:26][C:27]([F:28])([F:29])[F:30])=[C:20]([Br:19])[CH:21]=2)[N:32]=[N:33]1

Participants

8

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 2724141Tetrabutylammonium FluorideHCID 178506363HCID 178506363, compound

Product 2

HCID 18787018HCID 18787018, compoundYield 53%HCID 18787106HCID 18787106, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetra n-butyl ammonium fluoride solution (1M in THF, 12.5 ml, 12.5 mmol) was added over 5 minutes to a stirred solution of 4-[3-bromo-4-(trifluoromethoxy)phenyl]-1H-1,2,3-triazole (Description 59) (2.73 g, 8.85 mmol) and dimethyl sulfate (2.10 ml, 22.1 mmol) in THF (50 ml). The mixture was stirred for at room temperature for 1.5 hours, then water (100 ml) and diethyl ether (100 ml) were added. The layers were separated and the aqueous layer was extracted with ether (200 ml). The combined organic layers were washed with water (100 ml) and brine (100 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (75:25 increasing to 50:50) to give 2-methyl-4-[3-bromo-4-(trifluoromethoxy)phenyl]-2H-1,2,3-triazole as a colorless solid (1.50 g, 53%), 1H NMR (250 MHz, CDCl3) δ 8.07 (1H, d, J=2.1 Hz), 7.81 (1H, s), 7.73 (1H, dd, J=8.5, 2.1 Hz), 7.36 (1H, dq, J=8.5, 1.4 Hz), and 4.25 (3H, s), m/z (ES+) 322, 324 (M+1), and 1-methyl-4-[3-bromo-4-(trifluoromethoxy)phenyl]-1H-1,2,3-triazole as a colorless solid (566 mg, 20%), 1H NMR (250 MHz. CDCl3) d 8.12 (1H, d, J=2.1 Hz), 7.80 (1H, dd, J=8.5, 2.1 Hz), 7.78 (1H, s), 7.36 (1H, dq, J=8.5, 1.5 Hz), and 4.17 (3H, s), m/z (ES+) 322, 324 (M+1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ether (200 ml)
  3. washThe combined organic layers were washed with water (100 ml) and brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with hexane/EtOAc (75:25 increasing to 50:50)

Sources & evidence

ORD record
ord-2e1c51ef6cd44024ac61131c22446c57
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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