Ethyl Acetate → HCID 19436792, compound

HRID 1735017Notes

Reaction equation

HRID 1735017 reaction equation
CO[C:3]1[CH:4]=[C:5]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[N:7][CH:8]=1.P(Br)(Br)([Br:22])=O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Br:22][C:3]1[CH:4]=[C:5]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24613Phosphorus oxybromideHCID 19436789HCID 19436789, compound

Product 1

HCID 19436792HCID 19436792, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Methoxy-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy]pyridazine(Compound No. 5, 5.0 g, 0.0182 mole) and phosphorus oxybromide (5.7 g, 0.02 mole) were refluxed under N2 in toluene (100 mL) for 3.5 hours. The mixture was poured into ethyl acetate and extracted 2×200 mL with water. The organic layer was then extracted with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated in vacuo to give a crude oil. The oil was purified by chromatography on silica gel to give 5-bromo-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5yl]oxy]pyridazine (2.75 g, 47% yield) as a brown solid which was used directly in the following step.

Workup

  1. extractionextracted 2×200 mL with water
  2. extractionThe organic layer was then extracted with saturated sodium bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a crude oil
  7. customThe oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d86a6793da3f4624bb0e6e736c5810bf
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

Loading…