Hydrochloric Acid → 4-Chloro-2-fluoro-5-isopropoxy-nitrobenzene

HRID 35417Notes

Reaction equation

HRID 35417 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].I[CH:20]([CH3:22])[CH3:21].Cl>CC(C)=O>[Cl:1][C:2]1[C:3]([O:12][CH:20]([CH3:22])[CH3:21])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 131089864-Chloro-2-fluoro-5-isopropoxy-nitrobenzeneYield 91.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 15.8 g (0.083 mole) of 2-chloro-4-fluoro-5-nitrophenol in 90 mL of acetone was added 17.1 g (0.12 mole) of potassium carbonate followed by a solution of 21.0 g (0.12 mole) of 2-iodopropane in 10 mL of acetone. After complete addition, the reaction mixture was heated at 60° C. for approximately 18 hours. The mixture was cooled and poured into a mixture of ice and concentrated hydrochloric acid. The resultant mixture was extracted with ethyl acetate, and the extract was washed with a 1N sodium hydroxide solution. The washed extract was dried over anhydrous magnesium sulfate and was filtered. The solvent was evaporated under reduced pressure to leave 17.7 g of 4-chloro-2-fluoro-5-(1-methylethoxy)nitrobenzene as a solid.

Workup

  1. additionAfter complete addition
  2. temperatureThe mixture was cooled
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washthe extract was washed with a 1N sodium hydroxide solution
  5. extractionThe washed extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationwas filtered
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6a1d1b7f41cc4078a574d6eee7881fa9
Source dataset
uspto-grants-1988_08
Patent number
US04766233

Reaction notes

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