Stannous Chloride → 3,4-Bis(trifluoromethyl)aniline

HRID 54397

Reaction equation

HRID 54397 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N+:13]([O-])=O)[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10].Cl[Sn]Cl>C(O)C>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[C:9]([F:10])([F:11])[F:12])[NH2:13]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 27361664-Nitro-1,2-bis(trifluoromethyl)benzene

Product 1

HCID 15485793,4-Bis(trifluoromethyl)anilineYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 261 mg (1.00 mmol) of 3,4-bis(trifluoromethyl)nitrobenzene and 989 mg (5.23 mmol) of SnCl2 in 6 mL of ethanol was heated at 70° C. for 2 h. It was evaporated to dryness and the residue was treated with 1N NaOH to pH=13. White precipitate was observed. The mixture was extracted by CHCl3 (4×8 mL). The extract was dried (MgSO4) and evaporated to leave 228 mg (99%) of oil. 1H NMR (CDCl3), 4.167 (sb, 2), 6.803 (d, 1, J=7.41), 7.026 (s, 1), 7.579 (d, 1, J=8.58). 19F NMR (CDCl3), 55.014 (q, 3), 56.919 (q, 3).

Workup

  1. customIt was evaporated to dryness
  2. additionthe residue was treated with 1N NaOH to pH=13
  3. extractionThe mixture was extracted by CHCl3 (4×8 mL)
  4. dry with materialThe extract was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-3713417fb74441f18251fa41192506d9
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Linked notes

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