Stannous Chloride → 2-(Benzyloxy)-4-fluoroaniline

HRID 660827Notes

Reaction equation

HRID 660827 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 167713362-(Benzyloxy)-4-fluoroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-benzyloxy-4-fluoro-1-nitrobenzene (2.4 g, 10 mmol) in EtOH (20 mL) is added SnCl2 (9.45 g, 50 mmol) and the suspension is stirred at RT overnight. The solvent is removed under reduced pressure and the residue is adjusted to pH >8. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with water and brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give the product as a red oil.

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionThe aqueous layer is extracted with EtOAc
  3. washthe combined organic layers are washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-75440715f8304066b8180cb26d54d7b4
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…