Chlorosuccinimide → 2-Chloro-6-fluoro-4-(trifluoromethyl)aniline

HRID 1428998Notes

Reaction equation

HRID 1428998 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:5]1[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:2]([F:1])[C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 27376742-Fluoro-4-(trifluoromethyl)aniline

Product 1

HCID 199141572-Chloro-6-fluoro-4-(trifluoromethyl)anilineYield 70,666.898%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-fluoro-4-(trifluoromethyl)aniline (498 g, 2.783 mmol, 1.00 eq.) in acetonitrile (5 L) was added N-chlorosuccinimide (NCS, 408 g, 3.06 mmol, 1.1 eq.). Then the solution was heated under reflux for 3 hours and then concentrated under vacuum, diluted with petroleum ether (PE 1 L) and filtered. The filtrate was concentrated under vacuum to afford a red oil. The oily product was purified by vacuum distillation to give 2-chloro-6-fluoro-4-(trifluoromethyl)aniline as a yellow liquid (420 g, 71%).

Workup

  1. temperatureThen the solution was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated under vacuum
  4. additiondiluted with petroleum ether (PE 1 L)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customto afford a red oil
  8. distillationThe oily product was purified by vacuum distillation

Sources & evidence

ORD record
ord-518453cd77c84cc0832c6d20905f379e
Source dataset
uspto-grants-2015_01
Patent number
US08937185B2

Reaction notes

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