4-Bromophenylhydrazine hydrochloride → HCID 66749447, compound

HRID 1622862Notes

Reaction equation

HRID 1622862 reaction equation
[CH:1]1([C:4](=O)[CH2:5][C:6](=O)[C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:2]1.Cl.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1>CC(O)=O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:5][C:6]([C:7]([F:10])([F:9])[F:8])=[N:22]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 111946731-cyclopropyl-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 66749447HCID 66749447, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

1-Cyclopropyl-4,4,4-trifluorobutane-1,3-dione (1.330 g) was added to a mixture of (4-bromophenyl)hydrazine hydrochloride (1.65 g) and AcOH (10 ml). The mixture was stirred at 120° C. for 1 hr. AcOH was removed in vacuo and the residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give 1-(4-bromophenyl)-5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazole (2.2059 g) as a yellow oil.

Workup

  1. customAcOH was removed in vacuo
  2. customthe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-b90b5f19d7b54a25916fbb182ff56a7d
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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