Sodium Dithionite → 2-Amino-6-chloro-4-(trifluoromethyl)phenol

HRID 649098Notes

Reaction equation

HRID 649098 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([N+:20]([O-])=O)[C:11]=1[OH:23]>C(O)C.O>[NH2:20][C:12]1[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=[C:10]([Cl:9])[C:11]=1[OH:23]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 53828778HCID 53828778, compound

Product 1

HCID 212870732-Amino-6-chloro-4-(trifluoromethyl)phenol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Solid sodium dithionite (10 g) was added in portions to a stirred solution of 2-chloro-6-nitro-4-trifluoromethylphenol (4.5 g) in a mixture of ethanol (20 ml) and water (30 ml). The solution was stirred for 2 hours, left overnight, filtered, and evaporated. The residue was mixed with toluene and the toluene removed under reduced pressure. The residue was extracted with boiling chloroform (3×100 ml) and the chloroform extracts evaporated to give a yellow oil identified as the required substituted phenol.

Workup

  1. waitleft overnight
  2. filtrationfiltered
  3. customevaporated
  4. additionThe residue was mixed with toluene
  5. customthe toluene removed under reduced pressure
  6. extractionThe residue was extracted with boiling chloroform (3×100 ml)
  7. customthe chloroform extracts evaporated
  8. customto give a yellow oil

Sources & evidence

ORD record
ord-860de3247fae46ec987f818a8ff9fc4d
Source dataset
uspto-grants-1988_04
Patent number
US04738711

Reaction notes

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