Bromine → HCID 19751098, compound

HRID 466632Notes

Reaction equation

HRID 466632 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][CH:12]=[C:13]([C:19]([F:22])([F:21])[F:20])[C:14]=2[C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1>C(Cl)(Cl)Cl>[Br:1][C:12]1[NH:11][C:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)=[C:14]([C:15]([F:16])([F:17])[F:18])[C:13]=1[C:19]([F:22])([F:20])[F:21]

Participants

4

Reactant 2

HCID 24408BromineHCID 19103175HCID 19103175, compound

Product 1

HCID 19751098HCID 19751098, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Under a nitrogen purge, a solution of bromine (0.05 mL, 0.001 mol) and chloroform (5 mL) is added dropwise to a solution of 2-(p-chlorophenyl)-3,4-bis(trifluoromethyl)pyrrole (0.39 g, 0.001 mol) and chloroform (10 mL). The orange reaction mixture is stirred for 16 hours at room temperature then concentrated in vacuo to give an oil. The oil is extracted with methyl cyclohexane and the combined organic extracts are treated with carbon black and the solvent is removed in vacuo. The residue is dissolved in a small amount of hot hexane, decanted from insolubles and cooled in the freezer. Filtration of the cold solution gives the title compound as white crystals containing a half mole of HMPA (0.32 g mp 97°-100° C., 68%). Identified by IR and NMR spectral analyses.

Workup

  1. customUnder a nitrogen purge
  2. concentrationthen concentrated in vacuo
  3. customto give an oil
  4. extractionThe oil is extracted with methyl cyclohexane
  5. additionthe combined organic extracts are treated with carbon black
  6. customthe solvent is removed in vacuo
  7. dissolutionThe residue is dissolved in a small amount of hot hexane
  8. customdecanted from insolubles
  9. temperaturecooled in the freezer
  10. filtrationFiltration of the cold solution

Sources & evidence

ORD record
ord-2321eb87718e4778be70e41866eeb1fa
Source dataset
uspto-grants-1992_10
Patent number
US05157047

Reaction notes

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