Stannous Chloride → 2-Amino-5-(trifluoromethyl)phenol

HRID 1956620Notes

Reaction equation

HRID 1956620 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[OH:14])([O-])=O.Cl[Sn]Cl>CCO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:5]=1[OH:14]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 140916902-Nitro-5-(trifluoromethyl)phenol

Product 1

HCID 155242772-Amino-5-(trifluoromethyl)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-5-trifluoromethylphenol was prepared by treating 2-nitro-5-trifluoromethylphenol (500 mg, 2.41 mmol) with a solution of SnCl2 (3.5g, mmol) in EtOH at 23° C. for 12 h. The mixture was concentrated to 50 mL and adjusted to pH 7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J =8.5 Hz), 7.08(d, 1H, J=8.5 Hz)

Workup

  1. concentrationThe mixture was concentrated to 50 mL
  2. customThe reaction mixture was partitioned between H2O and EtOAc
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting colorless oil(370 mg, 87%) was used without further purification

Sources & evidence

ORD record
ord-1f0c5a4f21774317a60764479a4078b8
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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