2-(Trifluoromethyl)aniline → 2-Chloro-6-(trifluoromethyl)aniline

HRID 436344

Reaction equation

HRID 436344 reaction equation
NC1C=CC=CC=1C(F)(F)F.NC1C=CC(Cl)=CC=1C(F)(F)F.[NH2:24][C:25]1[C:30]([Cl:31])=[CH:29][C:28](Cl)=[CH:27][C:26]=1[C:33]([F:36])([F:35])[F:34]>>[NH2:24][C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[C:33]([F:36])([F:34])[F:35]

Participants

4

Reactant 3

HCID 69222-(Trifluoromethyl)anilineHCID 67961Benzenamine, 4-chloro-2-(trifluoromethyl)-HCID 12682552,4-Dichloro-6-(trifluoromethyl)aniline

Product 1

HCID 27563842-Chloro-6-(trifluoromethyl)aniline

Procedure

VPC assay of the organic product revealed the following composition (15% XE 60 column packing; 120° C-250° C; 4°/min.): o-aminobenzotrifluoride (13.1 wt. %; 25.94 grams; 0.161 mole; 83.9% conversion); 2-amino-5-chlorobenzotrifluoride, 53.5 wt. %; 105.9 grams or 64.5% corrected yield); and, 2-amino-3,5-dichlorobenzotrifluoride, 33.3 wt. %; 65.93 grams or 34.2% corrected yield). A trace of 2-amino-3-chlorobenzotrifluoride was produced.

Workup

  1. custom120° C-250° C
  2. custom105.9 grams or 64.5% corrected yield)
  3. custom65.93 grams or 34.2% corrected yield)

Sources & evidence

ORD record
ord-4ab88bc022c74ed3b3b8242e8e8c522a
Source dataset
uspto-grants-1977_02
Patent number
US04008278

Linked notes

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