Isoamyl Nitrite → 4-Bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazine

HRID 1184402Notes

Reaction equation

HRID 1184402 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[C:4](N)[CH:3]=1.C(ON=O)CC(C)C.C[Si](C)(C)[Br:25]>BrCBr>[Br:25][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 76113BromotrimethylsilaneHCID 866631346-Chloro-3-(2,2,2-trifluoroethoxy)pyridazin-4-amine

Product 1

HCID 866631334-Bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazineYield 23.8%

Reagents, catalysts & solvents 1

HCID 3024DibromomethaneSolvent

Procedure

To a suspension of 2.30 g 6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazin-4-ylamine in 23 ml dibromomethane was added 5.11 g isoamylnitrite at once and drop wise 4.642 g trimethylbromosilane at ambient temperature (during ca. 10 min). A moderate exotherm reaction was observed and a dark brown solution was obtained. The mixture was stirred at ambient temperature for 18 h. The solvents were evaporated and the residue was purified (3 times) by chromatography on silica gel using a gradient of heptane to dichloromethane to yield 0.70 g the title compound as white crystalline solid. MS (EI): 292 (M+H).

Workup

  1. customat ambient temperature
  2. custom(during ca. 10 min)
  3. customA moderate exotherm reaction
  4. customa dark brown solution was obtained
  5. customThe solvents were evaporated
  6. customthe residue was purified (3 times) by chromatography on silica gel using a gradient of heptane to dichloromethane

Sources & evidence

ORD record
ord-4e4e341978be48898de67c0576d08d10
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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