Hydrochloric Acid → HCID 15451886, compound

HRID 1637247Notes

Reaction equation

HRID 1637247 reaction equation
C(O)C.O.[Cl:5][C:6]1[CH:7]=[C:8]([N+:26]([O-])=O)[CH:9]=[C:10]([Cl:25])[C:11]=1[O:12][CH:13]([CH3:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17].Cl>C(O)C.[Fe]>[Cl:5][C:6]1[CH:7]=[C:8]([CH:9]=[C:10]([Cl:25])[C:11]=1[O:12][CH:13]([CH3:24])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:19])([F:18])[F:17])[NH2:26]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid3×HCID 19096565Water ethanolHCID 19348868HCID 19348868, compound

Product 1

HCID 15451886HCID 15451886, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent3×

Procedure

5.29 g iron filings, 240 mL of a 2/1 ethanol-water mixture, and 8.3 g 3,5-dichloro-4-(1-methyl-2,2,3,3,4,4,4-heptafluorobutoxy)nitrobenzene was stirred vigorously and heated under reflux while 2.0 mL conc. HCl in 2 mL ethanol was added dropwise. After one hour 2.0 mL conc. HCl in 2.0 mL ethanol was added and reflux was maintained for 6 hrs. Then added 2.0 mL conc. HCl in 3.0 mL ethanol and maintained reflux overnight. The mixture was filtered hot through Celite. The filtrate was concentrated under vacuum before being partitioned in saturated sodium bicarbonate and diethyl ether. The layers were separated and the aqueous layer was extracted with diethyl ether. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated to give 4.79 g of 3,5-Dichloro-4-(1-methyl-2,2,3,3,4,4,4-heptafluorobutoxy)aniline as an amber oil. 1H NMR and MS confirm pure product. Anal. calcd C11H8Cl2F7NO: C, 35.32; H, 2.16; N, 3.74. Found: C, 36.40; H, 2.33; N, 3.98.

Workup

  1. temperatureheated
  2. additionwas added dropwise
  3. temperaturereflux
  4. temperaturewas maintained for 6 hrs
  5. temperaturemaintained
  6. temperaturereflux overnight
  7. filtrationThe mixture was filtered hot through Celite
  8. concentrationThe filtrate was concentrated under vacuum
  9. custombefore being partitioned in saturated sodium bicarbonate
  10. customThe layers were separated
  11. extractionthe aqueous layer was extracted with diethyl ether
  12. washThe combined organics were washed with brine
  13. dry with materialdried (MgSO4)
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-613bf17a16394c17b4d6ba9ac3275981
Source dataset
uspto-grants-2000_03
Patent number
US06040345

Reaction notes

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