2-Benzylthio-4-(2-chloro-4-trifluoromethylphenoxy)nitrobenzene → 2-Benzylthio-4-(2-chloro-4-trifluoromethylphenoxy)aniline

HRID 64557Notes

Reaction equation

HRID 64557 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[Cl:26])[CH:12]=[CH:11][C:10]=1[N+:27]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])(O)O.[Na+]>C(O)C.[Pd]>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][C:17]=2[Cl:26])[CH:12]=[CH:11][C:10]=1[NH2:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 202362812-Benzylthio-4-(2-chloro-4-trifluoromethylphenoxy)nitrobenzeneHCID 23701735Sodium dihydrogen phosphite

Product 1

HCID 202362802-Benzylthio-4-(2-chloro-4-trifluoromethylphenoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2 g of 1B was dissolved in 30 ml of ethanol and 0.5 g of 5% palladium on carbon catalyst and 10% aqueous sodium dihydrogen phosphite added in portions until vigorous effervescence ceased. The reaction mixture was filtered, extracted with 400 ml of a 1:1 v:v mixture of ethylene dichloride/water, and the organic layer separated and dried. Chromatographic purification yielded 2-benzylthio-4-(2-chloro-4-trifluoromethylphenoxy)aniline (1C) as a brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted with 400 ml of a 1:1 v
  3. additionv mixture of ethylene dichloride/water
  4. customthe organic layer separated
  5. customdried
  6. customChromatographic purification

Sources & evidence

ORD record
ord-842fb3be1ead473aa9bb240c485de203
Source dataset
uspto-grants-1986_09
Patent number
US04609394

Reaction notes

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