Hydrochloric Acid → HCID 13564326, compound

HRID 637615Notes

Reaction equation

HRID 637615 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:7]=1.N([O-])=O.[Na+].[Cl:18][C:19]([Cl:21])=[CH2:20].C(=O)([O-])O.[Na+].[ClH:27]>C(OCC)(=O)C.CCCCCC.CC(C)=O>[F:13][C:5]1[CH:4]=[CH:3][C:2]([CH2:20][C:19]([Cl:27])([Cl:21])[Cl:18])=[CH:7][C:6]=1[CH:8]([CH3:12])[C:9]([OH:11])=[O:10]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6366Vinylidene chlorideHCID 516892Sodium BicarbonateHCID 13388011HCID 13388011, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13564326HCID 13564326, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 12 ml of 18% aqueous hydrochloric acid was dissolved 4 g of 2-(5-amino-2-fluorophenyl)propionic acid, and 4 ml of an aqueous solution of 1.1 g of sodium nitrite was added dropwise while maintaining the temperature between -15° C. and -10° C. The mixture was stirred for an hour, to which 40 ml of acetone, 8 g of 1,1-dichloroethylene, 1250 mg of sodium hydrogen carbonate and 400 mg of cupric chloride dihydrate were successively added. The mixture was gradually warmed up to room temperature and stirred overnight. The acetone layer was separated and the solvent was evaporated off. The residue was dissolved in ether, washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated off and the residue obtained was subjected to silica gel column chromatography (eluent: n-hexane--ethyl acetate=20:1) to afford 3.9 g of 2-[2-fluoro-5-(2,2,2-trichloroethyl)phenyl]propionic acid as an oily substance.

Workup

  1. additionwas added dropwise
  2. temperaturewhile maintaining the temperature between -15° C. and -10° C
  3. additionwere successively added
  4. customThe acetone layer was separated
  5. customthe solvent was evaporated off
  6. dissolutionThe residue was dissolved in ether
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated off
  10. customthe residue obtained

Sources & evidence

ORD record
ord-44706cdae0a44c5d9c4f8c91576d0d30
Source dataset
uspto-grants-1985_12
Patent number
US04557871

Reaction notes

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