Benzene → HCID 19841467, compound

HRID 1638745Notes

Reaction equation

HRID 1638745 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:18])[C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17])[NH2:5].[Cl:19]N1C(=O)CCC1=O.C1C=CC=CC=1>C(OCC)(=O)C.ClN1C(=O)CCC1=O>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[O:9][C:8]1[C:2]([Cl:1])=[CH:3][C:4]([NH2:5])=[C:6]([Cl:19])[C:7]=1[Cl:18]

Participants

6

Reactant 3

HCID 241BenzeneHCID 31398ChlorosuccinimideHCID 53633003HCID 53633003, compound

Product 1

HCID 19841467HCID 19841467, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 31398ChlorosuccinimideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a 300 milliliter round bottom reaction flask was charged 14.9 grams (51.4 mmol) of 3,5-dichloro-4-(2,4-difluorophenoxy) aniline, 7.2 grams (53.9 mmol) of N-chlorosuccinimide (NCS), and 100 milliliters of benzene. The reaction mixture was refluxed for 2 hours after which time additional NCS (350 milligrams, 2.6 mmol) was added. Reflux was then continued for an additional 1 hour. The mixture was allowed to cool, diluted with ethyl acetate (200 milliliters), washed with H2O, saturated NaHCO3 and brine; dried over Na2SO4 and concentrated under reduced pressure. The oily product obtained was purified by flash column chromatography (1:1 hexane toluene) to afford 4-(2,4-difluorophenoxy)-2,3,5-trichloroaniline (9.8 grams, 30.2 mmol, 59%) as a dark brown oil. The structure of this material was verified by its H'-NMR spectrum (CDCl3) 7.30-6.10 (m, 3H), 6.75 (s, 1H), 4.18 (br s, 2H).

Workup

  1. additionwas added
  2. temperatureReflux
  3. temperatureto cool
  4. washwashed with H2O, saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe oily product obtained
  8. customwas purified by flash column chromatography (1:1 hexane toluene)

Sources & evidence

ORD record
ord-ef4ae94c63434b068a9e0c6f8cb9f813
Source dataset
uspto-grants-1989_11
Patent number
US04880838

Reaction notes

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