Sodium Hydroxide → HCID 54435289, compound

HRID 1655551Notes

Reaction equation

HRID 1655551 reaction equation
Cl.Br[CH:3]([F:15])[C:4](F)([F:13])[O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.[OH-].[Na+]>[Zn].C(O)(=O)C>[F:13][C:4]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)=[CH:3][F:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19792701HCID 19792701, compound

Product 1

HCID 54435289HCID 54435289, compoundYield 107.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

4.05 g (61.2 mmol) of zinc dust was added to a mixture of 5.0 g (16.3 mmol) of p-(2-bromo-1,1,2-trifluoroethoxy)benzeneamine hydrochloride 5 ml of 6N5HCl and 45 ml of glacial acetic acid. The mixture was stirred at room temperature for 31/2 hours, then poured into ice, made basic with 50 percent aqueous NaOH and extracted two times into ether. The combined ether layers were washed with dilute aqueous NaOH, washed with water, dried over MgSO4 and filtered. HCl gas was bubbled into the solution. The resulting white solid was collected by filtration to give 3.0 g (88 percent of theoretical) of the above-named aniline as the hydrochloride salt along with a 10 percent impurity of 4-(1,1,2-trifluoroethoxy)benzeneamine.

Workup

  1. additionpoured into ice
  2. extractionextracted two times into ether
  3. washThe combined ether layers were washed with dilute aqueous NaOH
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customHCl gas was bubbled into the solution
  8. filtrationThe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-93ac94a398de4c86b760208d69924a6c
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Reaction notes

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