Tin tetrachloride → 4-(2,5-Dichlorophenoxy)-3-fluoroaniline

HRID 1993818Notes

Reaction equation

HRID 1993818 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[F:14].[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[F:14]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 597980461-(2,5-Dichloro-phenoxy)-2-fluoro-4-nitro-benzene

Product 1

HCID 289727064-(2,5-Dichlorophenoxy)-3-fluoroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(2,5-dichloro-phenoxy)-2-fluoro-4-nitro-benzene (0.5 g, 1.7 mmol) and tin chloride (1.57 g, 8.3 mmol) in 30 ml of anhydrous ethanol was heated to 70° C. under argon and stirred for 4 hours. The solution was allowed to cool and then poured into ice. The solution was made slightly basic (pH 7-8) by addition of saturated aqueous sodium bicarbonate solution, then extracted with ethyl acetate. The organic phase was thoroughly washed with brine and dried treated with anhydrous sodium sulfate. Evaporation of the solvent left a yellow oily product which was used for the next step without further purification.

Workup

  1. temperatureto cool
  2. additionpoured into ice
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was thoroughly washed with brine
  5. customdried
  6. additiontreated with anhydrous sodium sulfate
  7. customEvaporation of the solvent
  8. waitleft a yellow oily product which
  9. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-088607fcf1674831b4d0ede632494377
Source dataset
uspto-grants-2010_01
Patent number
US07652047B2

Reaction notes

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