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

HRID 712147Notes

Reaction equation

HRID 712147 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 1-benzyloxy-3-bromo-5-nitro-benzene (551 g, 1.78 mol) in THF (11 L) was added SnCl2.2H2O (2.17 kg, 9.62 mol) in one portion at rt. The reaction mixture was refluxed for 3 h. After completion of reaction (by TLC) the reaction mixture was cooled to 0-5° C. and basified with saturated NaHCO3 solution then extracted with EtOAc (4×5 L). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain a crude liquid product (480 g, 97%) that was carried forward to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customAfter completion of reaction (by TLC) the reaction mixture
  3. extractionthen extracted with EtOAc (4×5 L)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1cf0442a5bf47219ac8f828b4e9bc12
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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