N-bromobutanimide → HCID 19775929, compound

HRID 1612575Notes

Reaction equation

HRID 1612575 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=2)=[N:3]1.[Br:24]N1C(=O)CCC1=O>C(O)(=O)C.C(OC(=O)C)(=O)C>[Br:24][C:5]1[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=2)=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([F:8])([F:10])[F:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19775930HCID 19775930, compound

Product 1

HCID 19775929HCID 19775929, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-o-dinitrobenzene (17.7 g, 54.9 mmol) was dissolved in a mixture of glacial acetic acid (90 cm3) and acetic anhydride (10 cm3) and the solution was warmed to 80° C. N-Bromosuccinimide (14.7 g, 82.4 mmol) was added, and the mixture was stirred at 80° C. for 21 hours, and then cooled to room temperature. The precipitate was collected, washed with water, and then taken up in ethyl acetate (500 cm3). The solution was washed with saturated sodium bicarbonate solution (2×300 cm3), dried (MgSO4), filtered and evaporated under reduced pressure to give 4-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-o-dinitrobenzene (17.5 g) as a colourless solid m.p. 152°-153° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe precipitate was collected
  3. washwashed with water
  4. washThe solution was washed with saturated sodium bicarbonate solution (2×300 cm3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-53a352030e564f7fbc60910dc016acca
Source dataset
uspto-grants-1993_03
Patent number
US05190574

Reaction notes

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