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

HRID 358191Notes

Reaction equation

HRID 358191 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-d5c79f4840884e3eb3b7b10c99c40a3c
Source dataset
uspto-grants-1984_08
Patent number
US04465508

Reaction notes

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