Hydrochloric Acid → 2-Amino-6-fluoro-4-trifluoromethylphenol

HRID 2166795Notes

Reaction equation

HRID 2166795 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:5]=[C:6]([N+:9]([O-])=O)[C:7]=1[OH:8].O.S(S([O-])=O)([O-])=O.[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>O.C(O)C>[NH2:9][C:6]1[CH:5]=[C:4]([C:12]([F:15])([F:13])[F:14])[CH:3]=[C:2]([F:1])[C:7]=1[OH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 13013672HCID 13013672, compoundHCID 22707037Sodium dithionite hydrate

Product 1

HCID 130136732-Amino-6-fluoro-4-trifluoromethylphenol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product from (e) (4.1 g) in water (50 ml) was stirred vigorously while sodium dithionite hydrate (10 g) was added in portions. The mixture was stirred for 30 minutes and then ethanol (25 ml) and further sodium dithionite (5 g) were added. The mixture was stirred for another 15 minutes and then diluted to 400 ml, acidified (HCl) and extracted with dichloromethane (4×200 ml). The dichloromethane extract was dried (MgSO4) and evaporated to give a yellow oil which crystallised on cooling. This was identified as 3-amino-5-fluoro-4-hydroxybenzotrifluoride (2.9 g).

Workup

  1. additionwas added in portions
  2. stirringThe mixture was stirred for another 15 minutes
  3. additiondiluted to 400 ml
  4. extractionextracted with dichloromethane (4×200 ml)
  5. extractionThe dichloromethane extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated
  8. customto give a yellow oil which
  9. customcrystallised
  10. temperatureon cooling

Sources & evidence

ORD record
ord-938625adaefd4f11ba7e5480a4f5163f
Source dataset
uspto-grants-1983_06
Patent number
US04388472

Reaction notes

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