Hydrochloric Acid → HCID 19086722, compound

HRID 1464571Notes

Reaction equation

HRID 1464571 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([F:23])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1.O.Cl>C(O)(C)C>[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([F:23])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([NH2:12])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19086726HCID 19086726, compound

Product 1

HCID 19086722HCID 19086722, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-(2-Chloro-6-fluoro-4-trifluoromethylphenoxy)-2-nitrotoluene (5.57 g) and reduced iron powder (9.7 g) were suspended in isopropanol (73 cm3) and water (16 cm3) and concentrated hydrochloric acid (0.83 cm3) added. The mixture was stirred under reflux for 7 hours, cooled slightly and filtered through Hyflo. The filter pad was washed through with hot ethanol. The combined filtrate was evaporated to dryness, dissolved in ethyl acetate and washed with brine. The organic phase was dried (MgSO4), filtered and the filtrate evaporated to dryness to give a brown oil which was purified by flash chromatography (CHCl3) to give 4-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2-aminotoluene (4 g) as a pale brown oil. M+ =320

Workup

  1. temperatureunder reflux for 7 hours
  2. temperaturecooled slightly
  3. filtrationfiltered through Hyflo
  4. washThe filter pad was washed through with hot ethanol
  5. customThe combined filtrate was evaporated to dryness
  6. dissolutiondissolved in ethyl acetate
  7. washwashed with brine
  8. dry with materialThe organic phase was dried (MgSO4)
  9. filtrationfiltered
  10. customthe filtrate evaporated to dryness
  11. customto give a brown oil which
  12. customwas purified by flash chromatography (CHCl3)

Sources & evidence

ORD record
ord-ffff6900032a4bfc8e25bba1f877c31a
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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