Stannous chloride dihydrate → 3-(Benzyloxy)-5-bromoaniline

HRID 1399960Notes

Reaction equation

HRID 1399960 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[C:11]([Br:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[C:11]([Br:18])[CH:10]=1)[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 14784149HCID 14784149, compound

Product 1

HCID 578136263-(Benzyloxy)-5-bromoanilineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of iii (551 g, 1.78 mol) in THF (11 L) was added SnCl2.2H2O (2.17 kg, 9.62 mol) at RT. The mixture was refluxed for 3 h. The mixture was cooled to 0-5° C. and basified with saturated NaHCO3 solution and extracted with EtOAc (4×5 L). The combined organic layer were washed with brine, dried (Na2SO4), filtered and concentration in vacuo gave iv (480 g, 97%).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. extractionextracted with EtOAc (4×5 L)
  3. washThe combined organic layer were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-2ff02f12c1524e1b9a3c75ce844f12a0
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

Loading…