Water → 9H-Carbazole, 9-[4-(trifluoromethyl)phenyl]-

HRID 590001Notes

Reaction equation

HRID 590001 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.O.[Cl-].[NH4+:14].[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:14]2[C:6]3[CH:7]=[CH:2][CH:3]=[CH:4][C:21]=3[C:15]3[C:20]2=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 25517Ammonium Chloride

Product 1

HCID 114041419H-Carbazole, 9-[4-(trifluoromethyl)phenyl]-Yield 93.7%

Procedure

The reaction was conducted for 15 minutes in the same experimental procedures as in Example 1 except for using 4-chlorobenzotrifluoride (8.4 mL, 63.1 mmol, 1.0 equivalent) as an aryl halide. After cooling the reaction mixture to room temperature, to the mixture were added water (25 mL) and ammonium chloride (1.7 g). The aqueous layer was separated off, and the organic layer was concentrated under reduced pressure to give solid residue. The residue was dissolved in toluene, and the solution was decolorized by silica gel (1 g) and filtered through a Celite pad. The filtrate was concentrated under reduced pressure to give the solid, which was recrystallized from toluene/methanol to afford 18.4 g of N-(4-trifluoromethylphenyl)carbazole as a white powder.

Workup

  1. customThe aqueous layer was separated off
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customto give solid residue
  4. filtrationfiltered through a Celite pad
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give the solid, which
  7. customwas recrystallized from toluene/methanol

Sources & evidence

ORD record
ord-1f88142ed87248f59537580a7467e146
Source dataset
uspto-grants-2016_01
Patent number
US09233922B2

Reaction notes

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