Hydrochloric Acid → 2-[3-Fluoro-4-(2,2,2-trichloroethyl)phenyl]propionic acid

HRID 637612Notes

Reaction equation

HRID 637612 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[F:13].N([O-])=O.[Cl:17][C:18]([Cl:20])=[CH2:19].C(=O)([O-])O.[Na+].[ClH:26]>CCCCCC.O1CCOCC1.C(OCC)(=O)C.CC(C)=O>[F:13][C:3]1[CH:4]=[C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:7][C:2]=1[CH2:19][C:18]([Cl:26])([Cl:20])[Cl:17]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 946NitriteHCID 6366Vinylidene chlorideHCID 516892Sodium BicarbonateHCID 130652312-(4-Amino-3-fluorophenyl)propanoic acid

Product 1

HCID 135643242-[3-Fluoro-4-(2,2,2-trichloroethyl)phenyl]propionic acid

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

In 10 ml of a 17% aqueous hydrochloric acid solution was dissolved 2.5 g of 2-(4-amino-3-fluorophenyl)propionic acid. To the solution was added dropwise 5 ml of an aqueous solution of 1.04 g of sodiun nitrite at -15° C.--10° C. with stirring, and the reaction was carried out for an hour. To the mixture were added 25 ml of acetone and 3 g of 1,1-dichloroethylene at -10° C.--5° C., followed by 2.5 g of sodium hydrogen carbonate and 0.5 g of cupric chloride dihydrate. The mixture was gradually warmed up to room temperature and stirred at room temperature for 2 hours. Acetone was evaporated off and the residue was extracted with ether. The ether layer was washed with water and dried over anhydrous magnesium sulfate and the solvent was evaporated off. The residue thus obtained was subjected to silica gel column chromatography (eluent: ethyl acetate--dioxane--n-hexane=1:1:4) and recrystallized from n-hexane to obtain 2.3 g of 2-[3-fluoro-4-(2,2,2-trichloroethyl)phenyl]propionic acid, m.p. 92°-94° C.

Workup

  1. waitthe reaction was carried out for an hour
  2. stirringstirred at room temperature for 2 hours
  3. customAcetone was evaporated off
  4. extractionthe residue was extracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated off
  8. customThe residue thus obtained
  9. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-5b5518fb236e4e70898d154651973337
Source dataset
uspto-grants-1985_12
Patent number
US04557871

Reaction notes

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