Hydrochloric Acid → HCID 14100466, compound

HRID 648985Notes

Reaction equation

HRID 648985 reaction equation
Br[C:2]([F:19])([F:18])[C:3]([F:17])([F:16])[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH3:15].[Cl:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1.Cl>CS(C)=O.[Cu]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]([F:19])([F:18])[C:3]([F:17])([F:16])[O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=2[O:14][CH3:15])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 125101-Chloro-4-iodobenzeneHCID 14100465HCID 14100465, compound

Product 1

HCID 14100466HCID 14100466, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

Under a dry argon atmosphere a stirred mixture of 4-(2-bromo-1,1,2,2-tetrafluoroethoxy)-3-methoxynitrobenzene (5.0 g, 0.014 mole), 4-chloroiodobenzene (3.4 g, 0.014 mole), and copper powder (4.6 g, 0.072 mole, 200 mesh) in dimethyl sulfoxide (75 mL) was heated at about 160° C. for approximately three hours. The reaction mixture was allowed to cool to room temperature and stirred for an additional 18 hours. The cool mixture was poured into 200 mL of 2N hydrochloric acid, the resultant mixture was extracted with three 100 mL portions of methylene chloride. The extracts were combined and washed in succession with 2N hydrochloric acid, an aqueous, saturated, sodium chloride solution, and 2N aqueous sodium hydroxide. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving an oil. This oil was purified by column chromatography on silica gel, eluting with n-heptane:toluene (90:10), to yield 1.4 g of 4-[2-(4-chlorophenyl)-1,1,2,2-tetrafluoroethoxy]-3-methoxynitrobenzene as an oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe resultant mixture was extracted with three 100 mL portions of methylene chloride
  3. washwashed in succession with 2N hydrochloric acid
  4. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customleaving an oil
  8. customThis oil was purified by column chromatography on silica gel
  9. washeluting with n-heptane:toluene (90:10)

Sources & evidence

ORD record
ord-8d6e8cc62d5b44e283a41a0391726c2a
Source dataset
uspto-grants-1988_04
Patent number
US04737509

Reaction notes

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